- Preparation method of substituted benzene sulfonyl chloride
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The invention provides a preparation method of substituted benzene sulfonyl chloride, which comprises the following steps: carrying out diazotization reaction on an aniline compound with a structure as shown in a formula I to obtain fluoboric acid diazonium salt with a structure as shown in a formula II; obtaining substituted benzene sulfonyl chloride with a structure as shown in a formula III from the fluoboric acid diazonium salt with the structure as shown in the formula II; wherein R is selected from any one of ortho-chlorine, bromine, methyl, chloromethyl, bromomethyl, nitro, cyano, acetyl, meta-chlorine, bromine, methyl, chloromethyl, bromomethyl, nitro, cyano, acetyl, para-chlorine, bromine, methyl, chloromethyl, bromomethyl, nitro, cyano and acetyl. The preparation method of the substituted benzene sulfonyl chloride provided by the invention is simple in reaction process, easy to operate, ideal in effect and suitable for industrial production.
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Paragraph 0043-0046
(2021/05/08)
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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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- 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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- Orally active aminopyridines as inhibitors of tetrameric fructose-1,6-bisphosphatase
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A novel sulfonylureido pyridine series exemplified by compound 19 yielded potent inhibitors of FBPase showing significant glucose reduction and modest glycogen lowering in the acute db/db mouse model for Type-2 diabetes. Our inhibitors occupy the allosteric binding site and also extend into the dyad interface region of tetrameric FBPase.
- Hebeisen, Paul,Haap, Wolfgang,Kuhn, Bernd,Mohr, Peter,Wessel, Hans Peter,Zutter, Ulrich,Kirchner, Stephan,Ruf, Armin,Benz, J?rg,Joseph, Catherine,Alvarez-Sánchez, Rubén,Gubler, Marcel,Schott, Brigitte,Benardeau, Agnes,Tozzo, Effie,Kitas, Eric
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scheme or table
p. 3237 - 3242
(2011/07/07)
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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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- Phenylenediamine urotensin-II receptor antagonists and CCR-9 antagonists
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The present invention relates to urotensin II receptor antagonists, CCR-9 antagonists, pharmaceutical compositions containing them and their use.
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- Polymer electrolyte and process for producing the same
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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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- Elimination of substituted fluoren-9-ylmethyl benzenesulfonates: Hammett substituent effects at a mechanistic borderline
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Rates of elimination of fourteen substituted fluoren-9-ylmethyl benzenesulfonates have been measured in methanolic sodium methoxide and 90% aqueous ethanolic solutions of triethylamine, trimethylamine and 4-methyl morpholine. For the sodium methoxide, a linear Hammett plot with ρ = 0.74, consistent with reaction by an E2 mechanism, is observed. For the amine bases the Hammett plots are curved, suggesting a transition from an E2 mechanism for electron-withdrawing substituents to an irreversible E1cB mechanism with a smaller value of ρ for electron-donating substituents. The evidence for a change of mechanism is weakened by systematic and random deviations of substituents from correlations which span small changes in reactivity (less than ten-fold), by a surprisingly large value of ρ = 2 implied for the concerted (E2) reaction and by the possible influence of negative hyperconjugation. Nevertheless, it is consistent with independent evidence that the borderline between concerted and stepwise mechanisms is associated with chemically distinguishable reaction paths, even though pronounced carbanion character (and probably a small extent of bond-breaking to the leaving group) ensures a degree of similarity of structure and sensitivity to substituents of their transition states.
- Larkin, Finbar G.,More O'Ferrall, Rory A.,Murphy, Donal G.
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p. 1833 - 1848
(2007/10/03)
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- DISSOCIATION OF SUBSTITUTED BENZENESULPHONAMIDES IN WATER, METHANOL AND ETHANOL
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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
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p. 1182 - 1192
(2007/10/02)
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