- Facile synthesis of sulfonyl chlorides
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A method for the synthesis of sulfonyl chlorides and bromides from the corresponding sulfonate salts is described. The method gives good yields of the acid halides under very mild conditions, and is compatible with both acid and base sensitive functionalities.
- Huang, Jianxing,Widlanski, Theodore S.
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Read Online
- Method for continuously synthesizing paratoluensulfonyl chloride by using microchannel reactor
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The invention discloses a method for continuously synthesizing paratoluensulfonyl chloride by using a micro-channel reactor. The method comprises the following steps: by using alkyl halide as a solvent, toluene as a raw material, chlorosulfonic acid as a chlorosulfonating agent and a material obtained by mixing toluene, chlorosulfonic acid, alkyl halide and a catalyst as a reaction starting material, feeding the reaction starting material into a microchannel reactor, carrying out chlorosulfonation reaction, and performing post-treatment on a reaction product flowing out of the microchannel reactor to obtain paratoluensulfonyl chloride. According to the invention, continuous production of p-toluenesulfonyl chloride can be realized, the production efficiency can be greatly improved, and the output of waste acid can be greatly reduced.
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Paragraph 0058-0100
(2021/08/21)
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- Method for continuously synthesizing P-toluenesulfonyl chloride
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The method comprises the following steps: toluene, sulfur trioxide, chlorosulfonic acid, an organic base and a solvent are mixed in first static mixers, and then pumped into first microreactors to react. The first Micro-reactor outlet discharged first reaction mixture flows into second static mixer and mixed with sulfur trioxide, chlorosulfonic acid, low carbon chain fatty acid and solvent pumped into second static mixers respectively, and the resulting mixed materials are pumped into second microreactors to react. The second The secondary reaction mixture discharged from the microreactor was cooled, crystallized and isolated to yield p-toluenesulfonyl chloride as a product. To the method, the production efficiency is greatly improved; due to the addition of the sulfone inhibitor, the problems that a large amount of sulfone substances and polysulfonate are easily generated by sulfonation of sulfur trioxide are effectively solved, and hydrogen chloride gas is prevented from being generated.
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Paragraph 0089-0150
(2021/11/03)
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- Modulating optical and electrochemical properties of perylene dyes by twisting aromatic π-system structures
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Three highly fluorescent perylene bisimide dyes were synthesized, where aromatic π-system structures are twisted to different degree by steric hindrance of two or four substitution groups at bay position. Light-emitting colours of these dye solutions can be modulated from green, yellow to red, and their fluorescence quantum yields increase up to approximate 100% with increasing the π-system twisting, which can be considered for new class of wavelength-tunable dye lasers. π-Twisted dyes are more sensitive to microenvironment changes. Thus, they are better fluorescence probe and sensory materials than planar dyes. Electrochemical cyclic voltammetry measurements revealed that these dyes are suitable for n-type optoelectrical devices and materials. These dye solids display near infra-red emission at 600–850 nm. Owing to strong π-π stacking interaction, planar dye solid loses its outstanding optical properties compared to its solution. In contrast, π-twisted dye solids retain their excellent optical properties including narrow emission bands and relatively high fluorescence quantum yields due to the suppression of π-π stacking interaction. Exceptional fluorescence polarization phenomena were observed for these π-twisted dye solids. These optical results revealed that π-twisted perylene bisimide dyes are more excellent optical materials than planar dyes.
- Wang, Ying,Zhang, Qi,Gong, Junbo,Zhang, Xin
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- Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts
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We herein report a selective and catalytic C(sp3)-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp3)-H sulfonylation and thiolation and also exhibits good functional group tolerance.
- Chen, Guang-Le,He, Shi-Hui,Cheng, Liang,Liu, Feng
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supporting information
p. 8338 - 8342
(2021/10/25)
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- Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
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A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.
- Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
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- Investigation on recovery of p-mephso3k based on solid-liquid equilibrium of the p-mephso3k-k2co3-h2o system
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In this article, we propose a method of recovering p-MePhSO3K from the industrial by-product of quizalofop-p-ethyl. The phase diagram of the solid-liquid equilibrium system of p-MePhSO3K2CO3-H2O at the temperatures of 15, 25, 35, 45, and 55°C was determined and plotted. Based on the phase diagram of 25°C, the separation and recovery process of p-MePhSO3K from the p-MePhSO3K2CO3-H2O system was designed by analyzing the crystallization fields. First, p-MePhSO3K and K2CO3 were crystallized from wastewater in turn through evaporation separation. Then, the crystallized p-MePhSO3K was purified further by washing with ethanol. Finally, the pure p-MePhSO3K was transformed into the intermediate p-toluenesulfonyl chloride and then the intermediate L-p-toluenesulfonate ethyl lactate for quizalofop-p-ethyl production.
- Shuanghong, Hao,Jie, Xu,Mengqi, Chen,Yan, Wei
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p. 1249 - 1254
(2021/03/01)
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- Sulfonamide compound as well as preparation method and application thereof
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The invention discloses a sulfonamide compound as well as a preparation method and application thereof. Three kinases including EGFR, VEGFR-2 and FGFR1 are used as targets; chalcone is used as a primer; an alpha,beta-unsaturated carbonyl conjugated struct
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Paragraph 0034; 0035
(2020/05/05)
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- High yielding protocol for direct conversion of thiols to sulfonyl chlorides and sulfonamides
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In this paper, a new method for oxidative chlorination of thiols to sulfonyl chlorides and sulfonamides using H2O2 in the presence of TMSCl is reported. The excellent yields, short reaction times, excellent efficiencies, low costs, and easy separation of products are the most important advantages of this method.
- Sohrabnezhad, Samira,Bahrami, Kiumars,Hakimpoor, Farahman
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p. 256 - 264
(2019/02/06)
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- Preparation method of P-toluenesulfonyl chloride
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The invention discloses a preparation method of p-toluenesulfonyl chloride. The method comprises the following steps: mixing p-toluenesulfonate, a formamide catalyst, thionyl chloride and a solvent, and heating the mixture to 60 to 80 DEG C for reaction for 8 to 10 h, and then performing post-treatment to obtain the product p-toluenesulfonyl chloride. The method disclosed by the invention is highin catalytic performance by the adoption of a carboxamide catalyst, so that the reaction can be performed at a lower boiling point than thionyl chloride, thereby reducing the amount of the thionyl chloride; furthermore, the operation mode of directly mixing the materials at room temperature and heating the mixture for reaction is realized, and the safety of the reaction operation is improved; theproblems of material loss and environmental harm due to overflow of excessive sulfoxide chloride at high temperature in the reaction process of a reported mode are greatly reduced; and the preparationmethod is low in cost, environmentally friendly and extremely good in industrial application prospect.
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Paragraph 0022-0025
(2019/08/01)
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- Selective Late-Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by Pyry-BF4
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Reported here is a simple and practical functionalization of primary sulfonamides, by means of a pyrylium salt (Pyry-BF4), with nucleophiles. This simple reagent activates the poorly nucleophilic NH2 group in a sulfonamide, enabling the formation of one of the best electrophiles in organic synthesis: a sulfonyl chloride. Because of the variety of primary sulfonamides in pharmaceutical contexts, special attention has been focused on the direct conversion of densely functionalized primary sulfonamides by a late-stage formation of the corresponding sulfonyl chloride. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides, sulfonates, sulfides, sulfonyl fluorides, and sulfonic acids. The mild reaction conditions and the high selectivity of Pyry-BF4 towards NH2 groups permit the formation of sulfonyl chlorides in a late-stage fashion, tolerating a preponderance of sensitive functionalities.
- Gómez-Palomino, Alejandro,Cornella, Josep
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supporting information
p. 18235 - 18239
(2019/11/13)
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- Propanolysis of arenesulfonyl chlorides: Nucleophilic substitution at sulfonyl sulfur
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We have studied the mechanism of solvolysis of arenesulfonyl chlorides by propan-1-ol and propan-2-ol at 303-323 K. Kinetic profiles were appropriately fit by first-order kinetics. Reactivity increases with electron-donating substituents. Ortho-alkyl substituted derivatives of arenesulfonyl chlorides show increased reactivity, but the origin of this “positive” ortho-effect remains unclear. Likely, ortho-methyl groups restrict rotation around the C-S bond, facilitating the attack of the nucleophile. No relevant reactivity changes have been found with propan-1-ol and propan-2-ol in terms of nucleophile steric effect. The existence of isokinetic relationships for all substrates suggests a single mechanism for the series. Solvolysis reactions of all substrates in both alcohols show isokinetic temperatures (Tiso) close to the working temperature range, which is an evidence of the process being influenced by secondary reactivity factors, likely of steric nature in the TS. Solvation plays a relevant role in this reaction, modulating the reactivity. In some cases, the presence of t-Bu instead of Me in para- position leads to changes in the first solvation shell, increasing the energy of the reaction (ca. 1?kJ·mol?1). The obtained results suggest the same kinetic mechanism of solvolysis of arenesulfonyl chlorides for propan-1-ol and propan-2-ol, as in MeOH and EtOH, where bimolecular nucleophilic substitution (SN2) takes place with nucleophilic solvent assistance of one alcohol molecule and the participation of the solvent network involving solvent molecules of the first solvation shell.
- Iazykov, Mykyta,Canle, Moisés,Santaballa, J. Arturo,Rublova, Ludmila
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supporting information
(2017/09/08)
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- Design, synthesis and biological evaluation of novel phenylsulfonylurea derivatives as PI3K/mTOR dual inhibitors
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Five series of novel phenylsulfonylurea derivatives, 19a–d, 20a–d, 21a–d, 22a–d and 23a–d, bearing 4-phenylaminoquinoline scaffold were designed, synthesized and their IC50 values against four cancer cell lines (HepG-2, A549, PC-3 and MCF-7) were evaluated. Most compounds showed moderate cytotoxicity activity against the cancer cell lines. Structure–activity relationships (SARs) and pharmacological results indicated that introduction of 4-aminoquinoline scaffold and phenylsulfonylurea scaffold were beneficial for anti-tumor activity. Moreover, para-methoxyl substitution of 4-anilino moiety and para-halogen substitution of phenylsulfonylurea have different impacts on different series of compounds. Furthermore, the micromolecule group substitution in the 6-position of the quinoline ring have a slight impact on the cellular activity of the target compounds.
- Zhao, Bingbing,Lei, Fei,Wang, Caolin,Zhang, Binliang,Yang, Zunhua,Li, Wei,Zhu, Wufu,Xu, Shan
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- Conversion of thiols into sulfonyl halogenides under aerobic and metal-free conditions
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An environmentally benign, metal-free synthesis of sulfonyl chlorides and bromides from thiols in the presence of ammonium nitrate, an aqueous solution of HCl and HBr and oxygen as a terminal oxidant was developed. The reactivity of various substituted thiophenols, benzylic-, aliphatic- and heteroaromatic thiols was examined. Ammonium nitrate served as a source of nitrogen oxides (NO/NO2), which are the crucial players in a redox-catalytic cycle. Sulfonyl chlorides and bromides were isolated without extraction and "filtered" over a short pad of silica gel; the use of solvents was greatly reduced in comparison with traditional isolation and purification. A "one-pot" protocol for the conversion of thiol into sulfonamide is also demonstrated. Scale-up experiments on the preparation of sulfonyl chloride and bromide are shown. A possible reaction pathway is discussed.
- Jereb, Marjan,Hribernik, Luka
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supporting information
p. 2286 - 2295
(2017/07/24)
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- Sulfonyl halide synthesis by thiol oxyhalogenation using NBS/NCS – iPrOH
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A rapid and facile method provides a general route to sulfonyl bromides/chlorides by the oxidation of thiols using NXS – ROH (X?=?Br,Cl, R?=?iPr) as an oxyhalogenation reagent. Control experiments suggest that the alcohol component is the source of oxygen. The proposed method enable the access to structurally diverse sulfonyl bromides and chlorides including challenging examples, inaccessible by other synthetic methods.
- Silva-Cuevas, Carolina,Perez-Arrieta, Carlos,Polindara-García, Luis A.,Lujan-Montelongo, J. Armando
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supporting information
p. 2244 - 2247
(2017/05/16)
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- Step-by-step evaporation crystallization separation and recovery in the waste water and the toluene sulfonic acid potassium carbonate (by machine translation)
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The present invention (the name is: step-by-step evaporation crystallization separation and recovery of waste water in potassium carbonate and paratoluene sulfonic acid potassium) relates to a potassium carbonate, potassium bicarbonate and paratoluene sulfonic acid potassium separation and recovery process. This mixture can be separated by the following method: in the waste water with the potassium bicarbonate is added in equimolar potassium hydroxide, potassium carbonate is converted into potassium carbonate, then evaporate and a proper amount of water, lowering the temperature to the appropriate temperature constant temperature, filtering the insoluble solid is paratoluene sulfonic acid potassium, drying the spare; filter the resulting liquid to evaporate to dry, drying to obtain potassium carbonate. Recovering the resulting potassium P-toluenesulfonic acid in an appropriate solvent, under appropriate temperature, by reaction with the appropriate reagent to the toluene sulfonyl chloride, with L - lactic acid ethyl ester in the presence of an appropriate acid obtained by the reaction of L - lactic acid ethyl ester tosylates. (by machine translation)
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Paragraph 0009
(2017/07/26)
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- Aromatic Chlorosulfonylation by Photoredox Catalysis
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Visible-light photoredox catalysis enables the efficient synthesis of arenesulfonyl chlorides from anilines. The new protocol involves the convenient in situ preparation of arenediazonium salts (from anilines) and the reactive gases SO2and HCl (from aqueous SOCl2). The photocatalytic chlorosulfonylation operates at mild conditions (room temperature, acetonitrile/water) with low catalyst loading. Various functional groups are tolerated (e.g., halides, azides, nitro groups, CF3, SF5, esters, heteroarenes). Theoretical and experimental studies support a photoredox-catalysis mechanism.
- Májek, Michal,Neumeier, Michael,Jacobi von Wangelin, Axel
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p. 151 - 155
(2017/01/17)
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- Preparation method of p-toluene sulfonyl chloride
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A preparation method of p-toluene sulfonyl chloride comprises steps as follows: (1), p-toluene sulfonic acid is dissolved in chloroform, an ion liquid cosolvent is added, the mixture is uniformly stirred at the temperature of 0-40 DEG C, and chlorosulfuric acid is dropwise added; (2), after the chlorosulfuric acid is dropwise added, the mixture continues to react at a constant temperature for 1.5-4 h; (3), after the reaction ends, water is added to remove excessive chlorosulfuric acid, a liquid is separated in a separating funnel, and waste acid and an organic layer are obtained; (4), the organic layer is washed with water, a p-toluene sulfonic acid aqueous solution is extracted from an organic phase, wastewater is removed through liquid separation, and then a product layer is obtained; (5), chloroform is removed through distillation, and a finished p-toluene sulfonyl chloride product is obtained. A low-toxicity solvent, namely, chloroform is used, an ion liquid serves as cosolvent, p-toluene sulfonic acid and chlorosulfonic acid have an acyl chlorination reaction, after the reaction is performed to a certain degree, byproduct sulfuric acid and the organic layer are layered, the ion liquid cosolvent changes the distribution coefficient of p-toluene sulfonic acid, and accordingly, the yield of p-toluene sulfonyl chloride is increased.
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Paragraph 0034; 0035; 0013
(2016/11/28)
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- Aminoxidation of Arenethiols to N-Chloro-N-sulfonyl Sulfinamides
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A simple and efficient method to synthesize N-chloro-N-sulfonylsulfinamides by the direct aminoxidation of arenethiols under aqueous and mild conditions is disclosed, geminally installing the oxo and amino groups on the sulfur atom of arenethiols. The products have been primarily developed as sulfinylation reagents to convert Grignard reagents into sulfoxides, and as amination reagents to convert secondary amines into hydrazine derivatives.
- Yang, Zhanhui,Xu, Wei,Wu, Qiuyue,Xu, Jiaxi
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p. 3051 - 3057
(2016/04/26)
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- An efficient method for the preparation of sulfonyl chlorides: Reaction of disulfides or thiols with sodium hypochlorite pentahydrate (NaOCl·5H2O) crystals
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The reaction of disulfides or thiols with sodium hypochlorite pentahydrate in acetic acid efficiently provided the corresponding sulfonyl chlorides in high yields.
- Okada, Tomohide,Matsumuro, Hiroaki,Iwai, Toshiaki,Kitagawa, Saori,Yamazaki, Kento,Akiyama, Tomomi,Asawa, Tomotake,Sugiyama, Yukihiro,Kimura, Yoshikazu,Kirihara, Masayuki
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p. 185 - 187
(2015/02/19)
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- METHOD FOR PRODUCING SULFONYL CHLORIDE COMPOUNDS
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PROBLEM TO BE SOLVED: To provide a production method which enables safe and simple production of sulfonyl chloride compounds in high yields, which are useful as intermediates for medicines, agrochemicals, functional materials, and the like. SOLUTION: Provided is a method for producing sulfonyl chloride compounds comprising oxidation of thiols or disulfides in the presence of an oxidizing agent to produce sulfonyl chloride compounds. As the oxidizing agent is used sodium hypochlorite, and the reaction is performed with the pH of the reaction system adjusted to a neutral or acidic value of pH 7 or less. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0028; 0030
(2018/11/22)
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- New process for the production of arensulfonyl chloride from arensulfonic acid
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The present invention refers to degradation of a fine chemicals functionalised in a synthetic process of intermediates to conversion of an important role new manufacturing method relates to a novel process of arylsulfonyl, arylsulfonyl chloride hour draw from previous techniques are nick biting opinion gun method for producing [...] the users determine a structure of basic presents at 70 degree or more time and an elongated reactant hot reaction of undesirable and uniform reaction conditions to improve power efficiency nick biting opinion gun a dilute bis (trichloromethyl) polycarbonate and a catalytic amount of potassium and phosphoric acid incorporated tetrahedral amorphous [...] triethylamine and tree hereinafter also 25 reacting under a condition of gently arylsulfonyl chloride characterized by high yield in the dye by providing new method, pesticide, medicine, as well as related industrial electronic materials of the field will hole is compressed by the reciprocal movement.
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Paragraph 0026; 0027
(2016/12/26)
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- Synthesis of 3,3-dichloro-2-oxindoles from isatin-3-p-tosylhydrazones and (dichloroiodo)benzene
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Abstract A series of aryl- and N-substituted isatin derivatives were converted to the corresponding isatin-3-p-tosylhydrazones, and these were subjected to a Lewis base-catalyzed chlorination reaction that employs the hypervalent chlorinating agent PhICl2. The discovery of p-tosylhydrazones as chlorination precursors has expanded the functional group tolerance of the chlorination reaction to now include carbamates, acetamides, and sulfonates. Additionally, this allowed us to circumvent the use of the diazo group in our chlorination reaction, and offers a new avenue for exploring our two-step deoxygenative dihalogenation reaction. We also disclose the use of PhICl2 for the oxidative chlorination of sulfinates to the corresponding sulfonyl chlorides.
- Hepples, Charlotte,Murphy, Graham K.
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supporting information
p. 4971 - 4974
(2015/08/04)
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- Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/bromides using oxone-KX (X = Cl or Br) in water
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A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides by oxyhalogenation of thiols and disulfides with oxone-KX (X = Cl or Br) using water as the solvent is described. This journal is the Partner Organisations 2014.
- Madabhushi, Sridhar,Jillella, Raveendra,Sriramoju, Vinodkumar,Singh, Rajpal
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supporting information
p. 3125 - 3131
(2014/06/10)
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- Oxidation of disulfides with electrophilic halogenating reagents: Concise methods for preparation of thiosulfonates and sulfonyl halides
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The reaction of aromatic or benzylic disulfides with 2.5 equiv of Selectfluor in acetonitrile/water (10:1) at room temperature efficiently produced the corresponding thiosulfonates. Conversely, the reaction of disulfides with 6.5 equiv of Selectfluor or thiosulfonates with 4.5 equiv of Selectfluor in refluxing acetonitrile/water (10:1) provided sulfonyl fluorides in high yields. Accufluor and FP-T300 are also effective in preparing sulfonyl fluorides from disulfides under the similar reaction conditions. Sulfonyl chlorides or sulfonyl bromides were effectively obtained from the reaction of disulfides with 6 equiv of either N-chlorosuccinimide or N-bromosuccinimide in acetonitrile/water (10:1) at room temperature. Some other electrophilic chlorinating or brominating reagents are also able to be used instead of N-chlorosuccinimide or N-bromosuccinimide for the syntheses of sulfonyl halides from disulfides. These reactions of disulfides with electrophilic halogenating reagents are convenient methods to prepare thiosulfonates and sulfonyl halides.
- Kirihara, Masayuki,Naito, Sayuri,Nishimura, Yuki,Ishizuka, Yuki,Iwai, Toshiaki,Takeuchi, Haruka,Ogata, Tomomi,Hanai, Honoka,Kinoshita, Yukari,Kishida, Mari,Yamazaki, Kento,Noguchi, Takuya,Yamashoji, Shiro
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p. 2464 - 2471
(2014/04/03)
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- BIFUNCTIONAL HYDROXY-BISPHOSPHONIC ACID DERIVATIVES
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The present invention relates to a bifunctional hydroxy-bisphosphonic acid derivative of formula (I) below: or a pharmaceutically-acceptable salt thereof, a method for producing the same, pharmaceutical compositions containing the same, and the use thereof as a medicament, as well as a compound of formula (II) below: or a pharmaceutically-acceptable salt thereof, and the use thereof for producing a vectorized molecule of therapeutic or diagnostic purpose.
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Page/Page column
(2014/04/03)
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- Molecular design and synthesis of HCV inhibitors based on thiazolone scaffold
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A series of thiazolone derivatives was designed and synthesized as potential HCV NS5B allosteric polymerase inhibitors at the allosteric site thumb II. Their antiviral activity was evaluated and molecular modeling was utilized to give further envision on their probable binding modes in the allosteric binding site. Among the tested molecules, compound 9b displayed sub-micromolar inhibitory activity with an EC50 of 0.79 μM indicating excellent potency profile. It also showed good safety profile (CC50 ≥ 75 μM and SI ≥ 94.3).
- Al-Ansary, Ghada H.,Ismail, Mohamed A.H.,Abou El Ella, Dalal A.,Eid, Sameh,Abouzid, Khaled A.M.
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- One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, alcohols to bis(indolyl)methanes and synthesis of pyrroles catalyzed by N-chloro reagents
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A convenient synthesis of sulfonic esters from thiols and disulfides has been described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with Chloramin-T, tetra-butylammonium chloride (t-Bu4NCl) and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of bis(indolyl)methanes from alcohols using TCCA/KBr/wet-SiO2, and N-substituted pyrroles by reaction of hexane-2,5-dione with primary amines has been accomplished under mild condition with excellent yields.
- Veisi, Hojat,Ataee, Meral,Fatolahi, Leila,Lotfi, Shahram
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p. 111 - 117
(2013/07/26)
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- One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, and Paal-Knorr synthesis of pyrrole derivatives catalyzed by TCCA
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A convenient synthesis of sulfonic esters from thiols and disulfides is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with trichloroisocyanuric acid (TCCA), tetra-butylammonium chloride (t-Bu4NCl), and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of N-substituted pyrroles by the reaction of hexane-2,5-dione with primary amines has been accomplished using TCCA as a catalyst under mild condition with excellent yields.
- Hemmati, Saba,Mojtahedi, Mohammad Majid,Abaee, Mohammad Saeed,Vafajoo, Zahra,Saremi, Shokufe Ghahri,Noroozi, Mohammad,Sedrpoushan, Alireza,Ataee, Meral
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p. 347 - 357
(2013/09/23)
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- One-pot synthesis of sulfonamides and sulfonyl azides from thiols using chloramine-T
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A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols was accomplished by oxidation with chloramine-T (=N-chlorotosylamide=N-chloro-4- methylbenzenesulfonamide), tetrabutylammonium chloride (Bu4NCl), and H2O. The sulfonyl chlorides were then further allowed to react with excess amine or NaN3 in the same pot.
- Maleki, Behrooz,Hemmati, Saba,Tayebee, Reza,Salemi, Sirous,Farokhzad, Yasaman,Baghayeri, Mehdi,Zonoz, Farrokhzad Mohammadi,Akbarzadeh, Elahe,Moradi, Rohollah,Entezari, Azam,Abdi, Mohammad Reza,Ashrafi, Samaneh Sedigh,Taimazi, Fereshteh,Hashemi, Majid
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p. 2147 - 2151
(2013/12/04)
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- Synthesis of aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids
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A palladium-catalyzed method for the preparation of sulfonamides is described. The process exhibits significant functional group tolerance and allows for the preparation of a number of arylsulfonyl chlorides and sulfonamides under mild conditions.
- Debergh, J. Robb,Niljianskul, Nootaree,Buchwald, Stephen L.
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p. 10638 - 10641
(2013/08/23)
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- Trichloroisocyanuric acid (TCCA) and N-chlorosuccinimide (NCS) as efficient reagents for the direct oxidative conversion of thiols and disulfides to sulfonyl chlorides
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Trichloroisocyanuric acid (TCCA) and N-chlorosuccinimide (NCS) were found to be mild and efficient reagents for the direct oxidative conversion of sulfur compounds to the corresponding arenesulfonyl chlorides in good-to-excellent yields through the oxidative chlorination. The overall process is simple and practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides. Copyright
- Veisi, Hojat,Sedrpoushan, Alireza,Hemmati, Saba,Kordestani, Davood
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experimental part
p. 769 - 775
(2012/06/30)
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- Synthesis of sulfonyl chlorides and thiosulfonates from H2O 2-TiCl4
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A new method is described for the oxidative chlorination of thiols to sulfonyl chlorides using titanium tetrachloride in combination with the oxidant hydrogen peroxide. Direct conversion of thiols into their corresponding thiosulfonates is also reported. Good to excellent yields, short reaction times, high efficiencies, cost-effectiveness, and, facile isolation of the desired products make the present methodology a practical alternative.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Khaledian, Donya
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experimental part
p. 354 - 358
(2012/01/19)
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- Synthesis of sulfonyl chlorides and sulfonic acids in SDS micelles
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H2O2/POCl3 is found to be a reactive reagent system that can be used in sodium dodecyl sulfate (SDS) micellar solution in aqueous media for the direct oxidative chlorination of thiol and di-sulfide derivatives to give the desired sulfonyl chlorides. The oxidation of thiols and disulfides to sulfonic acids with this system is also reported. In most cases, these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity. Georg Thieme Verlag Stuttgart · New York.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Abbasi, Jamshid
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experimental part
p. 316 - 322
(2012/03/26)
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- Convenient one-pot synthesis of sulfonamides from thiols and disulfides using 1,3-dichloro-5,5-dimethylhydantoin (DCH)
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A convenient synthesis of sulfonamides from thiols and disulfides is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with 1,3-dichloro-5,5-dimethylhydantoin (DCH) under Nbenzyl-trimethylammonium chloride and water. The sulfonyl chlorides are then further allowed to react with excess amine in the same reaction vessel.
- Veisi, Hojat
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experimental part
p. 383 - 386
(2012/04/23)
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- Synthesis of sulfonamides and sulfonic esters via reaction of amines and phenols with thiols using H2O2-POCl3 system
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Phosphorus oxychloride efficiently promoted the synthesis of sulfonamides and sulfonic esters from thiols with hydrogen peroxide in the presence of Amberlite IRA-400 (OH-). This method has been applied to a variety of substrates including nucleophilic and sterically hindered amines, and also phenols with excellent yields of sulfonamides and sulfonic esters. In most cases these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Abbasi, Jamshid
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supporting information; experimental part
p. 5095 - 5101
(2012/07/28)
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- Poly(N,N'-Dichloro-N-ethyl-benzene-1,3-disulfonamide) and N,N,N',N'-Tetrachlorobenzene-1,3-disulfonamide as efficient reagents to direct oxidative conversion of thiols and disulfide to sulfonyl chlorides
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Poly(N,N'-Dichloro-N-ethyl-benzene-1,3-disulfonamide) (PCBS) and N,N,N',N'-Tetrachlorobenzene-1,3- disulfonamide (TCBDA) were found to be a mild and efficient reagent for the direct oxidative conversion of sulfur compounds to the corresponding arenesulfonyl chlorides in good to excellent yields through the oxidative chlorination. The overall process is simple, practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive, and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides.
- Veisi, Hojat,Ghorbani-Vaghei, Ramin,Mahmoodi, Jafar
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experimental part
p. 3692 - 3695
(2012/01/11)
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- Convenient one-pot synthesis of sulfonamides and sulfonyl azides from thiols using N -chlorosuccinimide
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A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with N-chlorosuccinimide (NCS), tetrabutylammonium chloride, and water. The sulfonyl chlorides are then further allowed to react with excess amine or sodium azide in the same reaction vessel. Georg Thieme Verlag Stuttgart - New York.
- Veisi, Hojat,Ghorbani-Vaghei, Ramin,Hemmati, Saba,Mahmoodi, Jafar
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experimental part
p. 2315 - 2320
(2011/10/13)
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- TAPC-promoted synthesis of sulfonyl chlorides from sulfonic acids
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A novel and efficient method is described for the preparation of sulfonyl chlorides from sulfonic acids using TAPC as chlorinating agent. Mild reaction conditions, shorter reaction times, high efficiencies, cost-effectiveness, and facile isolation of the desired products make the present methodology a practical alternative and will provide a valuable synthetic tool for various pharmaceutical applications. Georg Thieme Verlag Stuttgart · New York.
- Bahrami, Kiumars
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experimental part
p. 2671 - 2674
(2011/12/04)
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- Single-pot conversion of an acid to the corresponding 4-chlorobutyl ester
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A single pot conversion of carboxylic acids into the corresponding 4-chlorobutyl esters has been achieved by a novel procedure. The intermediate acid chlorides are not isolated. The double bond and aromatic methoxy group survive the mild reaction conditions. In almost all the examples studied the products are purified by simple flash chromatography.
- Pal, Sutanuka,Pal, Sudhir Chandra
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experimental part
p. 596 - 599
(2012/04/18)
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- DABCO-bis (sulfur dioxide), DABSO, as a convenient source of sulfur dioxide for organic synthesis: Utility in sulfonamide and sulfamide preparation
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The charge-transfer complex generated from the combination of DABCO and sulfur dioxide, DABSO, is a bench-stable colorless solid suitable for use in organic synthesis as a replacement for gaseous sulfur dioxide. The complex can be combined with Grignard reagents to form sulfinates, which can then be converted in situ to a series of sulfonamides. Alternatively, reaction with anilines and iodine leads to the formation of a series of sulfamides. Cheletropic addition between DABSO and 2,3-dimethylbutadiene provides the corresponding sulfolene.
- Woolven, Holly,Gonzalez-Rodriguez, Carlos,Marco, Isabel,Thompson, Amber L.,Willis, Michael C.
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supporting information; experimental part
p. 4876 - 4878
(2011/12/05)
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- A simple and highly effective oxidative chlorination protocol for the preparation of arenesulfonyl chlorides
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2,4-Dichloro-5,5-dimethylhydantoin (DCDMH) was found to be a mild and efficient reagent for the direct oxidative conversion of sulfur compounds to the corresponding arenesulfonyl chlorides in good to excellent yields through oxidative chlorination. The method is suitable for many types of sulfur substrates (thiols, disulfides, and benzylic sulfides). The overall process is simple, practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides.
- Pu, Yu-Ming,Christesen, Alan,Ku, Yi-Yin
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supporting information; experimental part
p. 418 - 421
(2010/03/04)
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- 4-[1-(Substituted aryl/alkyl carbonyl)-benzoimidazol-2-yl]-benzenesulfonic acids: Synthesis, antimicrobial activity, QSAR studies, and antiviral evaluation
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A series of 4-[1-(substituted aryl/alkyl carbonyl)-benzoimidazol-2-yl]- benzene sulphonic acids (1-20) was synthesized and evaluated, in vitro, for their antimicrobial activity and the results indicated that compounds 4-[1-(4-Nitrobenzoyl)-1H-benzoimidazol-2-yl]-benzenesulfonic acid (9) and 4-(1-octadec-9-enoyl-1H-benzoimidazol-2-yl)-benzenesulfonic acid (18) were found to be the most active ones. QSAR investigations indicated that the multi-target QSAR model was effective in describing the antimicrobial activity over the one-target QSAR models. Further the mt-QSAR model indicated the importance of the topological parameter, Balaban index (J) followed by the electronic parameter, LUMO and topological parameter, valence second order molecular connectivity index (2χv) in describing the antimicrobial activity of synthesized compounds (1-20).
- Yadav, Snehlata,Kumar, Pradeep,De Clercq, Erik,Balzarini, Jan,Pannecouque, Christophe,Dewan, Sharwan Kumar,Narasimhan, Balasubramanian
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scheme or table
p. 5985 - 5997
(2011/01/13)
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- A convenient, one-pot procedure for the preparation of acyl and sulfonyl fluorides using Cl3CCN, Ph3P, and TBAF(t -BuOH) 4
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Various carboxylic acids were converted into acyl fluorides in excellent yields by treatment with trichloroacetonitrile, triphenylphosphine, and TBAF(t-BuOH)4 at room temperature. The reaction was applicable to the preparation of acid-sensitive amino acid fluorides without deprotection or rearrangement
- Kim, Joong-Gon,Jang, Doo Ok
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experimental part
p. 3049 - 3052
(2011/02/25)
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- Iron-mediated radical halo-nitration of alkenes
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Radical halo-nitration of alkenes using iron(III) nitrate nonahydrate and halogen salt has been developed. The present reaction proceeds by radical addition of nitrogen dioxide generated by thermal decomposition of iron(III) nitrate nonahydrate and subsequent trapping of the resultant radical by a halogen atom in the presence of halogen salt. Application of this method to synthesis of nitroalkenes is also described. The practicality of the present method using nontoxic and inexpensive iron reagents has been shown by the application to broad alkenes.
- Taniguchi, Tsuyoshi,Fujii, Tatsuya,Ishibashi, Hiroyuki
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scheme or table
p. 8126 - 8132
(2011/03/17)
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- A new effective synthesis of arene mono- and disulfonyl chlorides
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Arene mono- and disulfonyl chlorides have been easily synthesized starting from the corresponding anilines via aqueous oxidative chlorination of S-aryl O-ethyl dithiocarbonates intermediates, aryl methyl sulfides, or from arenethiols. Georg Thieme Verlag Stuttgart.
- Barbero, Margherita,Bazzi, Stefano,Cadamuro, Silvano,Dughera, Stefano,Magistris, Claudio,Venturello, Paolo
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supporting information; experimental part
p. 1803 - 1806
(2010/10/20)
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- A novel, practical synthesis of sulfonyl chlorides from thiol and disulfide derivatives
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Hydrogen peroxide, in the presence of zirconium tetrachloride, is a very efficient reagent for the direct oxidative conversion of thiol and disulfide derivatives into the corresponding sulfonyl chlorides with high purity through oxidative chlorination. Excellent yields, very short reaction times, mild reaction conditions, and the avoidance of harsh reagents are the main advantages of this method.
- Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Soheilizad, Mehdi
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experimental part
p. 2773 - 2776
(2010/02/28)
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- Direct conversion of thiols to sulfonyl chlorides and sulfonamides
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(Chemical Equation Presented) H2O2 in combination with SOCl2 proved to be a highly reactive reagent for the direct oxidative conversion of thiol derivatives to the corresponding sulfonyl chlorides with high purity through oxidative chlorination. Upon reaction with amines, the corresponding sulfonamides were obtained in excellent yields and in very short reaction times.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Soheilizad, Mehdi
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supporting information; experimental part
p. 9287 - 9291
(2010/03/04)
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- (Arylsulfonyl)acetones and -acetonitriles: New activated methylenic building blocks for synthesis of 1,2,3-triazoles
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β-Keto sulfones and b-nitrile sulfones were used as building blocks for 1,2,3-triazole synthesis in the Dimroth cyclization. It was shown, that sulfone reagents undergo base-catalyzed cyclization under mild conditions (at room temperature) to give 1,2,3-triazoles in moderate to excellent yields. This fact has confirmed the high nucleophilicity of sulfonylmethylenic compounds and allows new synthetic applications. Georg Thieme Verlag Stuttgart.
- Pokhodylo, Nazariy T.,Matiychuk, Vasyl S.,Obushak, Mykola D.
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scheme or table
p. 2321 - 2323
(2010/02/16)
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- One-Pot synthesis of sulfonamides from primary and secondary amine derived sulfonate salts using cyanuric chloride
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A convenient, mild and efficient one-pot synthesis of new sulfonamides is described. The reaction of primary or secondary amine derived sulfonate salts in the presence of cyanuric chloride, triethylamine as base, and anhydrous acetonitrile as solvent at room temperature gives the corresponding sulfonamides in good to excellent yields. Georg Thieme Verlag Stuttgart.
- Rad, Mohammad Navid Soltani,Khalafi-Nezhad, Ali,Asrari, Zeinab,Behrouz, Somayeh,Amini, Zohreh,Behrouz, Marzieh
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experimental part
p. 3983 - 3988
(2010/03/26)
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