98-66-8Relevant academic research and scientific papers
Cornforth and Corey-Suggs reagents as efficient catalysts for sulfonation of aromatic and heteroaromatic compounds using NaHSO3 under solvent free and microwave conditions
Fatima, Touheeth,Duguta, Govardhan,Purugula, Venkanna,Yelike, Hemanth Sriram,Kamatala, Chinna Rajanna
, p. 1001 - 1006 (2020/07/27)
Cornforth and Corey-Suggs reagents Pyridinium Dichromate (PDC) and Pyridinium Chlorochromate (PCC) were explored as efficient catalysts for sulfonation of aromatic and heteroaromatic compounds using NaHSO3 in aqueous acetonitrile medium at room temperature within 1–4 h, while microwave assisted reactions took place within 1–4 min under solvent-free conditions. These observations indicate significant rate accelerations in microwave assisted reactions. which were explained due to the bulk activation of molecules induced by insitu generated high temperatures and pressures when microwaves are transmitted through reaction medium.
Aryl and alkyl sulfonic acid compounds as well as construction method adopting inorganic sulfur salt and application
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Paragraph 0046-0049; 0072-0075, (2020/09/16)
The invention discloses aryl and alkyl sulfonic acid compounds as shown in a formula (1) and a synthesis method thereof. The method comprises the following step: aromatic iodine and an inorganic sulfur source or alkyl bromide and an inorganic sulfur source as reaction raw materials react in a solvent under the action of alkali, a catalyst or an additive to obtain a series of aryl and alkyl sulfonic acid compounds. According to the method, the aryl and alkyl sulfonic acid compounds are constructed in one step by taking an inorganic sulfur reagent as a sulfur source, so that the defect of the mode in which the aryl and alkyl sulfonic acid compounds are synthesized by taking concentrated sulfuric acid, chlorosulfonic acid or sulfur dioxide gas and the like as sulfonating reagents in the priorart is avoided. The aryl and alkyl sulfonic acid compounds developed by the invention can be used for synthesizing aryl and alkyl sulfonic acid drug analogues.
Sustainable access to sulfonic acids from halides and thiourea dioxide with air
Zhang, Hui,Wang, Ming,Jiang, Xuefeng
supporting information, p. 8238 - 8242 (2020/12/29)
A sustainable and mild one-step strategy is explored for the synthesis of aryl and alkyl sulfonic acids using a facile combination of halides and sulfur dioxide surrogates under air. The cheap industrial material thiourea dioxide was employed as an eco-friendly and easy-handling sulfur dioxide surrogate, while air was used as a green oxidant. Both aryl and alkyl sulfonic acids were obtained under transition metal-catalyzed or transition metal-free conditions. Mechanistic studies demonstrated that sulfinate was involved as an intermediate in this transformation. Notably, this protocol has been applied to the late-stage sulfonation of the drugs naproxen, isoxepac and ibuprofen.
Regioselective Sulfonation of Aromatic Compounds over 1,3-Disulfonic Acid Imidazolium Chloride under Aqueous Media
Moosavi-Zare, Ahmad Reza,Zolfigol, Mohammad Ali,Noroozizadeh, Ehsan
, p. 1682 - 1684 (2016/07/06)
1,3-Disulfonic acid imidazolium chloride ([Dsim]Cl), as a Bronsted acidic ionic liquid, is introduced for the sulfonation of aromatic compounds by in situ generation of sulfuric acid at 50 °C under mild conditions and in aqueous medium.
Nucleophilic Substitution Reactions of 2,4-Dinitrophenyl X-Substituted-Benzenesulfonates and Y-Substituted-Phenyl 4-Nitrobenzenesulfonates with Azide Ion: Regioselectivity and Reaction Mechanism
Moon, Ji-Hyun,Kim, Min-Young,Han, So-Yeop,Um, Ik-Hwan
, p. 1360 - 1365 (2015/07/15)
The second-order rate constants for reactions of 2,4-dinitrophenyl X-substituted-benzenesulfonates (4a-4f) and Y-substituted-phenyl-4-nitrobenzenesulfonates (5a-5f) with N3- ion have been measured spectrophotometrically. The reactions of 4a-4f proceed through S-O and C-O bond fission pathways competitively. Fraction of the S-O bond fission decreases rapidly as the substituent X in the benzenesulfonyl moiety changes from an electron-withdrawing group to an electron-donating group. The Hammett plots for reactions of 4a-4f are linear with ρX=1.87 and 0.56 for the S-O and C-O bond fission, respectively. The fact that the substituent X is further away from the reaction site of the C-O bond fission than that of the S-O bond fission is one reason for the smaller ρX value. The nature of the reaction mechanism (i.e., a stepwise mechanism in which expulsion of the leaving group occurs after the rate-determining step) is also responsible for the smaller ρX value obtained from the C-O bond fission. The Bronsted-type plot for the reactions of 5a-5f is linear with βlg=-0.63, which is typical for reactions reported previously to proceed through a concerted mechanism. Effects of substituents X and Y on regioselectivity and reaction mechanism are discussed in detail.
A PROCESS FOR MANUFACTURING HALOARYL COMPOUNDS FROM MIXTURES OF ISOMERS OF DIHALODIARYLSULFONES
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Page/Page column 18; 19, (2013/07/05)
A process for the manufacture of a haloaryl compound which comprises contacting a mixture of dihalodiarylsulfone isomers [mixture (M)] with sulfuric acid to provide a mixture of haloarylsulfonic acid isomers [mixture (M1)] and reacting mixture (M1) in the presence of water. The process is independent on the manufacturing process of mixture (M) and is advantageous in that the obtained haloaryl compound can be recycled to the first step of a dihalodiarylsulfone manufacturing process.
Synthesis of sulfonyl chlorides and sulfonic acids in SDS micelles
Bahrami, Kiumars,Khodaei, Mohammad M.,Abbasi, Jamshid
experimental part, p. 316 - 322 (2012/03/26)
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.
PROCESS FOR PREPARING 4,4'-DICHLORODIPHENYL SULFONE
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Page/Page column 4, (2011/11/06)
The invention relates to a process for preparing 4,4′-dichlorodiphenyl sulfone, comprising the reaction of monochlorobenzene and liquid sulfur trioxide, wherein the liquid sulfur trioxide used has a boron content of at most 100 ppm based on the total weight of the sulfur trioxide used, including all secondary components.
PROCESS FOR PREPARING 4,4'-DICHLORODIPHENYL SULFONE
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Page/Page column 4, (2011/11/06)
The invention relates to a process for preparing 4,4′-dichlorodiphenyl sulfone proceeding from monochlorobenzene, wherein the content in the monochlorobenzene used of hydrocarbons having from 5 to 8 carbon atoms is at most 100 ppm; based on the total weight of the monochlorobenzene used, including the secondary components. The present invention further relates to the use of monochlorobenzene with the properties mentioned for preparation of 4,4′-dichlorodiphenyl sulfone.
The mechanisms of acid-catalyzed hydrolysis of n-(4-substituted arylthio) phthalimides
Kutuk, Halil,Yakan, Hasan
experimental part, p. 1460 - 1469 (2011/10/05)
The acid-catalyzed hydrolysis of N-(4-substitutedarylthio)phthalimides was studied in aqueous solutions of sulfuric, perchloric, and hydrochloric acids at 40.0 ±0.1° C. Analysis of the data by the excess acidity method, activation parameters, and substituent effects indicates hydrolysis by an A-2 mechanism at low acidity. At higher acidities, a changeover to an A-1 mechanism is observed.
