cas 98-60-2, 4-Chlorobenzenesulfonyl chloride

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Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
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
(2021/09/20)

NEW SELECTIVE MODULATORS OF INSECT NICOTINIC ACETYLCHOLINE RECEPTORS
The present invention relates to a compound having the following formula (I): wherein: - A is a (hetero)aryl radical comprising from 5 to 10 carbon atoms, possibly substituted by at least one substituent chosen from the group consisting of: halogen atoms, amino, azido, cyano, nitro, hydroxyl, formyl, carboxyl, amido, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, alkenyl groups, cycloalkenyl groups, and alkynyl groups, and - R is H, CN or CF3, or their pharmaceutically acceptable salts, racemates, diastereomers or enantiomers.
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(2020/06/01)

Preparation method of medical intermediate of parachlorobenzenesulfonyl chloride
The invention discloses a preparation method of a medical intermediate of parachlorobenzenesulfonyl chloride. The preparation method specifically comprises the following steps: firstly, cyclodextrin is modified sequentially through maleic anhydride and tetradecyl trimethyl ammonium chloride, and the modified cyclodextrin is obtained; and then a reaction is conducted by adopting sodium 4-chlorobenzenesulfonate and thionyl chloride as raw materials and the modified cyclodextrin as a catalyst, and by being added with ammonium trifluoroacetate for assisting. The prepared medical intermediate of the parachlorobenzenesulfonyl chloride is high in yield and high in purity, the reacting conditions are easy to operate, the requirements for equipment are low, and control is easy.
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(2019/03/08)

High yielding protocol for direct conversion of thiols to sulfonyl chlorides and sulfonamides
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
p. 256 - 264
(2019/02/06)

Design, synthesis and biological evaluation of novel phenylsulfonylurea derivatives as PI3K/mTOR dual inhibitors
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
(2018/07/13)

Preparation method of 4-chlorothiophenol
The invention relates to a simple preparation method of 4-chlorothiophenol. 4-chlorobenzenesulfonyl chloride is prepared from sodium 4-chlorobenzenesulfonate and thionyl chloride as raw materials andtoluene as a solvent through a reaction at 50-70 DEG C for 3-5 h under the action of a phase transfer catalyst and reduced by iron powder at the temperature of 40-60 DEG C under an acidic condition, and 4-chlorothiophenol is obtained. The method has the characteristics of being low in cost, simple and convenient to operate and suitable for industrial production.
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Paragraph 0016; 0018

(2018/04/26)

The sulfonylurea-containing structure of the preparation and application of zola non-nepal derivatives (by machine translation)
The invention discloses a sulfonylurea structure containing sorafenib derivative, its geometric isomer and pharmaceutically acceptable salt, hydrate, solvate or prodrug, and application thereof in preparation of drugs treating and/or preventing hyperplastic diseases, application in preparation of drugs treating and/or preventing cancers, and application in preparation of drugs treating and/or preventing lung cancer, liver cancer, gastric cancer, colon cancer and breast cancer.
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(2017/08/26)

Conversion of thiols into sulfonyl halogenides under aerobic and metal-free conditions
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
supporting information
p. 2286 - 2295
(2017/07/24)

Aromatic Chlorosulfonylation by Photoredox Catalysis
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
p. 151 - 155
(2017/01/17)

Sulfonyl halide synthesis by thiol oxyhalogenation using NBS/NCS – iPrOH
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
supporting information
p. 2244 - 2247
(2017/05/16)

Aminoxidation of Arenethiols to N-Chloro-N-sulfonyl Sulfinamides
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
p. 3051 - 3057
(2016/04/26)

A process for the preparation of substituted benzene sulfonyl chloride
The invention provides a preparation method of a pesticide intermediate, and in particular relates to a preparation method of substituted benzene sulfonyl chloride. The preparation method comprises the following steps: by taking substituted aniline as a raw material, first, carrying out diazo-reaction with sodium nitrite; then, carrying out chlorosulfonation with thionyl chloride aqueous liquor containing a catalyst to prepare substituted benzene sulfonyl chloride, wherein the yield ranges from 78% to 91%. The preparation method provided by the invention simplifies the reaction step, is safe to operate, mild in reaction conditions which are easy to control and low in equipment demand, the yield is improved, the production cost is lowered, emission of the three wastes is reduced, and the environment-friendly load is reduced, so that the preparation method is suitable for industrialized production.
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Paragraph 0030; 0031; 0032

(2017/03/08)

New synthetic sulfone derivatives inhibit growth, adhesion and the leucine arylamidase APE2 gene expression of Candida albicans in vitro
The successful preventing and effective treatment of invasive Candida albicans infections required research focused on synthesis of new classes of agents and antifungal activity studies. Bromodichloromethyl-4-chloro-3-nitrophenyl sulfone (named compound 6); dichloromethyl-4-chloro-3-nitrophenyl sulfone (named 7); and chlorodibromomethyl-4-hydrazino-3-nitrophenyl sulfone (named 11) on inhibition of planktonic cells' growth, leucine arylamidase APE2 gene expression, and adhesion to epithelial cells were investigated. In vitro anti-Candida activities were determined against wild-types, and the morphogenesis mutants: Δefg1 and Δcph1. MICs of compounds 6, 7 and 11 (concentrated at 0.25-16 μg/ml) were determined using the Clinical and Laboratory Standards Institute Broth Microdilution Method (M27-A3 Document). APE2 expression was analyzed using RT-PCR; relative quantification was normalized against ACT1 in cells growth in YEPD and on Caco-2 cell line. Adherence assay of C. albicans to Caco-2 was performed in 24-well-plate. The structure activity relationship suggested that sulfone containing hydrazine function at C-1 (compound 11) showed higher antifungal activity (cell inhibition% = 100 at 1-16 μg/ml) than the remaining sulfones with chlorine at C-1. Δcph1/Δefg1 was highly sensitive to compound 11, while the sensitivity was reduced in Δcph1/Δefg1::EFG1 (% = 100 at 16-fold higher concentration). Compound 11 significantly affected adherence to epithelium (P ≤0.05) and hyphae formation. The APE2 up-regulation plays role in sulfones' resistance on MAP kinase pathway. Either CPH1 or EFG1 play a role in the resistance mechanism in sulfones. The strain-dependent phenomenon is a factor in the sulfone resistance mechanism. Sulfones' mode of action was attributed to reduced virulence arsenal in terms of adhesiveness and pathogenic potential related to the APE2 expression and morphogenesis.
Staniszewska, Monika,Bondaryk, Ma?gorzata,Ochal, Zbigniew
supporting information
p. 314 - 321
(2015/03/04)

An efficient method for the preparation of sulfonyl chlorides: Reaction of disulfides or thiols with sodium hypochlorite pentahydrate (NaOCl·5H2O) crystals
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
p. 185 - 187
(2015/02/19)

METHOD FOR PRODUCING SULFONYL CHLORIDE COMPOUNDS
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 0031; 0033

(2018/11/22)

Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/bromides using oxone-KX (X = Cl or Br) in water
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
p. 3125 - 3131
(2014/06/10)

Oxidation of disulfides with electrophilic halogenating reagents: Concise methods for preparation of thiosulfonates and sulfonyl halides
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
p. 2464 - 2471
(2014/04/03)

Molecular design and synthesis of HCV inhibitors based on thiazolone scaffold
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.
p. 19 - 32
(2013/10/01)

One-pot synthesis of sulfonamides and sulfonyl azides from thiols using chloramine-T
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
p. 2147 - 2151
(2013/12/04)

Synthesis of sulfonyl chlorides and sulfonic acids in SDS micelles
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
experimental part
p. 316 - 322
(2012/03/26)

Synthesis of sulfonyl chlorides and thiosulfonates from H2O 2-TiCl4
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
experimental part
p. 354 - 358
(2012/01/19)

TAPC-promoted synthesis of sulfonyl chlorides from sulfonic acids
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
experimental part
p. 2671 - 2674
(2011/12/04)

Convenient one-pot synthesis of sulfonamides and sulfonyl azides from thiols using N -chlorosuccinimide
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
experimental part
p. 2315 - 2320
(2011/10/13)

A simple and highly effective oxidative chlorination protocol for the preparation of arenesulfonyl chlorides
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
supporting information; experimental part
p. 418 - 421
(2010/03/04)

A new effective synthesis of arene mono- and disulfonyl chlorides
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
supporting information; experimental part
p. 1803 - 1806
(2010/10/20)

Aqueous process chemistry: The preparation of aryl sulfonyl chlorides
The use of aqueous acidic conditions for the preparation of arylsulfonyl chlorides from diazonium salts in the presence of copper salts, preferably CuCl, together with thionyl chloride as the sulfur dioxide source, has considerable advantages over recommended literature procedures, whereby reactions are carried out in acetic acid with minimisation of water content of the solvent. The method has been shown to be successful for a wide range of electron-deficient and electron-neutral aryl substrates. The sulfonyl chlorides are protected from hydrolysis by their low solubility in water, which results in their direct precipitation from the reaction mixture in good yields (>70%) and high strength (>98% w/w). The aqueous process, which is additionally safer and more robust, can be readily scaled up and has significant environmental benefits.
Hogan, Philip J.,Cox, Brian G.
experimental part
p. 875 - 879
(2010/04/22)

(Arylsulfonyl)acetones and -acetonitriles: New activated methylenic building blocks for synthesis of 1,2,3-triazoles
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.
scheme or table
p. 2321 - 2323
(2010/02/16)

Chlorotrimethylsilane-nitrate salts as oxidants: Direct oxidative conversion of thiols and disulfides to sulfonyl chlorides
(Chemical Equation Presented) A mixture of nitrate salt and chlorotrimethylsilane is found to be a mild and efficient reagent for the direct oxidative conversion of thiols (1) and disulfides (2) to the corresponding sulfonyl chlorides (3) in excellent yields through oxidative chlorination. Sulfides and sulfoxides were also found to undergo oxidation to sulfones under similar reaction conditions. In most cases these reactions are highly selective, simple, and clean, affording products in high yield and purity.
Prakash, G. K. Surya,Mathew, Thomas,Panja, Chiradeep,Olah, George A.
p. 5847 - 5850
(2008/02/09)

Sulfonyl chloride formation from thiol derivatives by N-chlorosuccinimide mediated oxidation
Oxidation of several thiol derivatives by a combination of N-chlorosuccinimide and dilute hydrochloric acid proceeded smoothly, affording the corresponding sulfonyl chlorides in good yield. Georg Thieme Verlag Stuttgart.
Nishiguchi, Atsuko,Maeda, Kazuhiro,Miki, Shokyo
p. 4131 - 4134
(2008/03/13)

Phenylenediamine urotensin-II receptor antagonists and CCR-9 antagonists
The present invention relates to urotensin II receptor antagonists, CCR-9 antagonists, pharmaceutical compositions containing them and their use.
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(2008/06/13)

Effect of para substitution on dissociation of N-phenylbenzenesulfonamides
The reaction of substituted anilines and benzenesulfonyl chlorides has been used to prepare 49 substituted N-phenylbenzenesulfonamides of general formula 4-X-C6H4SO2NHC6H4-Y- 4′. Their purity was checked by elemental analysis. The substituents X and Y include H, CH3, CH3O, Cl, Br, CN, and NO2. The dissociation constants of all compounds were determined by potentiometric titration in methanol, acetonitrile, N,N-dimethylformamide, and pyridine. The obtained dissociation constants, pKHA, were correlated with various sets of substituent constants. It was found that the effects of substituents X and Y on the dissociation are best described by using the Hammett equation with σp constants and the Yukawa-Tsuno equation with σp- and σp constants, respectively. This result confirms the direct conjugation of Y substituent with the reaction centre. The explained variability using the additive model was above 96% in all the solvents used. The data also provided information about the transmission effect of the SO2 group. The average dissociation constants were further processed by the latent variables methods, principal components and conjugated deviations analyses.
Mansfeld, Martin,Parik, Patrik,Ludwig, Miroslav
p. 1479 - 1490
(2007/10/03)

A new, mild preparation of sulfonyl chlorides
A new method was developed for the preparation of sulfonyl chlorides from sulfonic acids under neutral conditions using 2,4,6-trichloro-1,3,5-triazine as chlorinating agent.
Blotny, Grzegorz
p. 1499 - 1501
(2007/10/03)

Process for functionalising a phenolic compound carrying an electron-donating group
The invention concerns a method for functionalizing a phenolic compound bearing an electron-donor group, in said group para position, inter alia a method for the amidoalkylation of a phenolic compound bearing an electron-donor group, and more particularly, a phenolic compound bearing an electron-donor group preferably, in the hydroxyl group ortho position. The method for functionalizing in para position with respect to an electron-donor group carried by a phenolic compound is characterised in that the phenolic compound bearing an electron-donor group is subjected to the following steps: a first step which consists of protecting the hydroxyl group in the form of a sulphonic ester function; a second step which consists in reacting the protected phenolic compound with an electrophilic reagent; optionally, a third step deprotecting the hydroxyl group.
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(2008/06/13)

Polymer electrolyte and process for producing the same
A polymer electrolyte having, in a main chain, a structural unit represented by the following formula (1):-[Ar1-(SO2-N-(X+)-SO2-Ar2)m-SO2-N-(X+)-SO2-Ar1-O]- wherein Ar1 and Ar2 independently represent a divalent aromatic groups, m represents an integer of 0 to 3, and X+ represents an ion selected from hydrogen ion, an alkali metal ion and ammonium ion, which is excellent in proton conductivity, thermal resistance and strength. The polymer electrolyte is soluble in solvents and has excellent film forming property and recycling efficiency.
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(2008/06/13)

Bispiperidines as antithrombotic agents
Novel compounds which are inhibitors of the binding of fibrinogen to the Gp IIb/IIIa platelet receptors, and which can be used therepeutically as antithrombotic agents
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(2008/06/13)

Effects of medium and substituents on dissociation of 4,4′-disubstituted bis(benzenesulfon)imides
Ten 4,4′-disubstituted bis(arenesulfon)imides of the general formula XC6H4SO2NHSO2C6H 4X have been synthesized and their structures confirmed by their 1H NMR spectra. Elemental analyses are presented for the compounds not yet described. The dissociation constants of these model substances have been measured potentiometrically in pyridine, dimethylformamide, methanol, ethanol, propylene carbonate, acetone, acetonitrile, 1,2-dichloroethane and tetramethylene sulfone. The pKHA values obtained have been correlated with three sets of the Hammett substituent constants and the results have been used to discuss the solvent and substituent effects on the dissociation of the compounds studied. Sulfonimides with electron-acceptor substituents behave as rather strong acids in some solvents (pyridine, dimethylformamide, methanol and ethanol), whereas normal substituent dependences are found in other solvents. The experimental data have also been interpreted with the help of the statistical methods based on latent variables. From the calculations it follows that only the first principal component, which correlates well with the substituent constant sets adopted, is statistically significant in describing the substituent effect on the acid-base process studied.
Ludwig, Miroslav,Stverka, Pavel
p. 1205 - 1214
(2007/10/03)

Process for the preparation of aromatic sulfonyl chlorides
A process for the preparation of aromatic sulfonyl chlorides of the formula I STR1 in which R1, R2 and R3 are identical or different and are hydrogen, fluorine, chlorine, bromine or iodine atoms, alkyl(C1 -C4), acetamido, nitro or carboxyl groups, or R1 and R2 together form an aromatic or heteroaromatic ring having 5 or 6 ring members, which can be substituted by fluorine, chlorine, bromine or iodine atoms, alkyl(C1 -C4), acetamido, nitro or carboxyl groups, by reaction of aromatic compounds of the formula II STR2 in which R1, R2 and R3 have the abovementioned meanings, with chlorosulfonic acid in excess or with chlorosulfonic acid or oleum and thionyl chloride, by reacting in the presence of sulfamic acid as a catalyst.
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(2008/06/13)

Preparation of 2-chloro-5-methyl-pyridine
A process for the preparation of 2-chloro-5-methylpyridine of the formula STR1 which comprises reacting 3-methyl-pyridine-1-oxide of the formula STR2 with a chlorinating agent of the formula STR3 in which R1 represents alkyl, halogenoalkyl, cycloalkyl, optionally substituted aryl, NR2 R3 or OR4 in which R2 and R3 individually represent alkyl, cycloalkyl or aryl or together represent alkanediyl or oxaalkanediyl and R4 represents alkyl, cycloalkyl or optionally substituted aryl, in the presence of a basic organic nitrogen compound and in the presence of a diluent at a temperature between about -20° C. and +150° C.
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(2008/06/13)

Convenient One-Pot Synthesis of Sulfonyl Chlorides from Thiols Using Sulfuryl Chloride and Metal Nitrate
Various sulfonyl chlorides were obtained in excellent yields by the reaction of alkyl and aryl thiols with sulfuryl chloride in the presence of metal nitrate under mild condition in aprotic solvents such as acetonitrile and N,N-dimethylformamide.
Park, Young Jun,Shin, Hyun Ho,Kim, Yong Hae
p. 1483 - 1486
(2007/10/02)

LEUKOTRIENE-INHIBITING SUBSTITUTED (QUINOLIN-2-YL-METHOXY)PHENYL-N,N'-SULPHONYLUREAS AND USE THEREAS
Lipoxygenase-inhibiting and leukotriene-inhibiting substituted (quinolin-2-yl-methoxy)phenyl-N,N'-sulphonylureas of the formula and physiologically acceptable salts thereof
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(2008/06/13)

Multiple Structure-Reactivity Relationships for a Menschutkin-type SN2 Reaction
The mechanism of nucleophilic displacement was studied by using three variable systems of ρX, ρY and ρZ obtained from the change of substituents X, Y and Z for the reaction of (Z)-substituted benzyl (X)-benzenesulphonates with (Y)-substituted N,N-dimethylanilines in aceton at 35 deg C.The coefficient of the interaction term, ρXY, has a value of 0.21 which means that bond-making and -breaking are concerted in the SN2 transition state.In the range Z = H to p-NO2, in which the SN2 mechanism is predicted to be dominant, the ρZY value is very large, 0.5, which means that the interaction between Z and Y is very large. ρZX is ca. 0.06 which means that the interaction is small between X and Z.In contrast, in the range Z = H to p-Me, in which the SN1 mechanism is dominant, the ρZY value is nearly zero, indicating no interaction between Z and Y.Changes of substituent effect and interaction terms, ρXY, ρYZ and ρZX are useful tools for distinguishing wrong reaction mechanisms.
Yoh, Soo-Dong,Tsuno, Yuho,Fujio, Mizue,Sawada, Masami,Yukawa, Yasuhide
p. 7 - 14
(2007/10/02)

Chroman derivatives for combating thrombosis and asthma
For inhibiting thombocyte aggregation, vasodilating and bronchodilating, the new chroman derivatives of the formula STR1 in which R1 stands for hydrogen, halogen, alkyl, hydroxyl, alkoxy, trifluoromethyl or cyano, R2 and R3 are identical or different and stand for hydrogen, alkyl, cycloalkyl or aryl, R4 stands for hydroxyl, alkoxy, aryloxy, aralkoxy or for a group of the formula --NR5 R6, where R5 and R6 are identical or different and in each case denote hydrogen, alkyl, aryl or aralkyl, X denotes a direct bond or an oxygen or sulphur atom, NH or N-alkyl, and n denotes 0 or 1, and their physiologically tolerable salts. Also new intermediates of the formulas STR2
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(2008/06/13)

A KINETIC STUDY OF THE FRIEDEL-CRAFTS REACTION OF NAPHTHALENE WITH PARA- SUBSTITUTED BENZENESULPHONYL CHLORIDES: THE EFFECT OF THE SUBSTITUENT
The kinetics of the Friedel-Crafts reaction of naphthalene with para-substituted benzenesulphonyl chlorides have been investigated.The rate constants for equations (i) (formation of the sulphonyl cation) and (ii) (sulphone formation) were determined separately.The effect of the para-substituents on k1 was XC6H4SO2Cl + AlCl3 XC6H4SO2+*AlCl4- , XC6H4SO24*AlCl4- + C10H8 XC6H4SO2C10H7*AlCl3 + HCl well expressed by Yukawa-Tsuno equation, log(k1X/K1H)= ρ1(Δ?R(+))> where ρ1= -2.7 and γ1= 0.4.On the other hand, the effect of the para-substituents on k3(=k1k2/k-1) was expressed by the Brown-Okamoto equation, log(k3X/k3H)= ρ3?+ where ρ3= -2.8.Thus, the electron-donating para-substituents gave the greater reaction rates.We concluded that the sulphonyl cation gives large negative ρ values as a result of its high reactivity, and that its low selectivity for α-attack is due to a steric effect.These kinetic results have been rationalised in terms of bifunctional acid-base catalysis in phenylsulphonnylation.
Yoshii, Yoshihiro,Ito, Akiyoshi,Hirashima, Tsuneaki,Shinkai, Seiji,Manabe, Osamu
p. 777 - 782
(2007/10/02)

Influence of Pressure on the Menschutkin-Type Reaction of Phenethyl Arenesulfonates with Pyridine
Kinetic investigation of β-phenethyl arenesulfonates with pyridine in acetonitrile revealed that the rates of these reactions which were lower than those of the reaction of benzyl benzenesulfonate with pyridine in acetone were increased with raising temperatures and pressures.The activation volumes were comparable to those of benzyl system, but the activation entropies were negatively larger than those of benzyl system.From these phenomena it can be deduced that phenethyl system has more SN2 character in the transition state, comparing with the reaction of benzyl system.With raising pressures the Hammett reaction parameters (ρ) were decreased, indicating that the reaction is probably closer to the tihgt SN2 character at higher pressures.
Yoh, Soo-Dong,Park, Jong-Hwan,Lee, Kyung-A,Han, In-Sook
p. 1149 - 1152
(2007/10/02)

REACTIONS OF SULFINYL CHLORIDES WITH 1,3-ENYNIC SILAHYDROCARBONS
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Vorob'eva, I. S.,Stadnichuk, M. D.
p. 1843 - 1852
(2007/10/02)

SELECTIVE PRODUCTION OF p-DICHLOROBENZENE FROM CHLOROBENZENE
The possibility of selective production of p-dichlorobenzene was investigated via the process of decomposition of p-chlorobenzenesulfonyl chloride, obtained by selective chlorosulfonation of chlorobenzene, in sulfuryl chloride solution in the presence of 2,2'-azo-bis(isobutyronitrile) (AIBN) and hexamethylenetetramine (hexamine, methenamine).The optimal parameters of the chlorosulfonation and the decomposition were determined.It was found by kinetic measurements that the role of hexamethylenetetramine in the decomposition by sulfuryl chloride of p-chlorobenzenesulfonyl chloride is the acceleration of the thermal dissociation of AIBN.The order of the overall decomposition reaction and its apparent activation energy have been determined.This latter value is 87.51 kJ mol-1.The activation energy of the dissociation of AIBN calculated from the experimental decomposition curves of p-chlorobenzenesulfonyl chloride is less than that given in the literature for the spontaneous thermal dissociation of AIBN.This fact also supports the accelerating effect of hexamethylenetetramine.
Buzas, I.,Szotyory, L.,Ujhidy, A.
p. 353 - 360
(2007/10/02)

DISSOCIATION OF SUBSTITUTED BENZENESULPHONAMIDES IN WATER, METHANOL AND ETHANOL
Thirteen monosubstituted arylsulphonamides (XC6H4SO2NH2) and two 3,4-disubstituted arylsulphonamides (X2C6H3SO2NH2) have been synthetized and their dissociation constants have been measured by potentiometric titration in water, methanol, and ethanol.The Hammett substitution dependences have been calculated for all the media, and changes in the reaction constants due to transition from water to alcohols are discussed in confrontation with analogous dependences of benzoic acids.The reaction constant ρ found in methanol is lower than that in water.The dissociation constants have been treated by the method of the principal components and by multiple linear regression.
Ludwig, Miroslav,Pytela, Oldrich,Kalfus, Karel,Vecera, Miroslav
p. 1182 - 1192
(2007/10/02)

A Convenient Preparation of Arenesulfonyl Chlorides from the Sodium Sulfonates and Phosphoryl Chloride/Sulfolane
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Fujita, Shinsaku
p. 423 - 424
(2007/10/02)

Process for preparing 4-4'-dichlorodiphenyl sulphone
A process is provided for producing 4,4'-dichlorodiphenyl sulfone, which comprises the steps of (a) reacting a monochlorobenzene with sulfur trioxide in the presence of at least 15 mole percent to 50 mole percent of thionyl chloride, based on the sulfur trioxide, at a temperature from the freezing point of the reactants to 40°C; (b) adding to the reaction mixture of step (a) at least 60 mole percent thionyl chloride, based on the sulfur trioxide, and preferably a small catalytic amount of dimethylformamide, wherein the total thionyl chloride in the reaction mixture is at least 110 mole percent. based on the sulfur trioxide, while maintaining the reaction mixture at a temperature between 25°C. and 70°C.; (c) continuing the reaction up to a temperature of 160°C and then d) reacting the products of step (c) with monochlorobenzene in the presence of ferric chloride catalyst to produce 4,4'-dichlorodiphenyl sulfone.
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(2008/06/13)

KINETICS OF THE TRANSFORMATIONS OF AROMATIC SULFO DERIVATIVES TO ACID HALIDES IN CHLORO- AND FLUOROSULFONIC ACID MEDIA
The pseudofirst-order rate constants for the formation of the corresponding sulfonic acid halides (keff) from sulfo derivatives with the general formula RC6H4SO3X, where X = NH2, Cl, F, and R = H, p-Cl, p-NO2, and m-NO2, were measured by GLC in fluorosulfonic and chlorosulfonic acids.The effect of substituents in the benzene ring on the rate of the transformations of the sulfo derivatives into the halides is similar to the previously investigated effect of substituents on the rate of solvolysis of substituted benzenesulfonyl halides in 100percent sulfuric acid (ρ -4).Com parison of the ratios of the keff values for the transformations of the sulfonamides in chlorosulfonic and fluorosulfonic acids and also the sulfonyl fluorides in 100percent sulfuric acid and chlorosulfonic acid with the ratios of the acidities of the respective media shows that these reactions have acid-catalytic character.The sulfonyl chlorides and sulfonamides in 100percent sulfuric acid are solvolyzed to a significant degree with the participation of H2S2O7.
Ivanov, S. N.,Gnedin, B. G.
p. 1909 - 1914
(2007/10/02)