Optimization of the synthesis conditions of products formed in arenesulfonylation of N-alkylated anilines

Optimization of the synthesis conditions of products formed in arenesulfonylation of N-alkylated... Fundamental kinetic aspects of the arenesulfonylation of N-alkylated anilines in aqueous-organic media, the nonaqueous component of which are alcohols, ethers, and acetonitrile were studied. It was shown that, with increasing fraction of water in the solvent, the reaction rate constant grows and the reactivity of N-alkyl anilines depends not only on the structure of the alkyl radical, but also on the content of water in the solvent. It was found that dimethyl sulfoxide has a catalytic effect on these processes. The strategy of choosing the medium in syntheses of biologically active sulfonyl derivatives of fatty-aromatic amines is discussed. A conclusion about the applicability of aqueous-organic media in the production technology of N-alkylated anilines is based on a calculation of the yield of their arenesulfonylation products. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Russian Journal of Applied Chemistry Springer Journals

Optimization of the synthesis conditions of products formed in arenesulfonylation of N-alkylated anilines

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Publisher
Springer Journals
Copyright
Copyright © 2014 by Pleiades Publishing, Ltd.
Subject
Chemistry; Chemistry/Food Science, general; Industrial Chemistry/Chemical Engineering
ISSN
1070-4272
eISSN
1608-3296
D.O.I.
10.1134/S1070427214090146
Publisher site
See Article on Publisher Site

Abstract

Fundamental kinetic aspects of the arenesulfonylation of N-alkylated anilines in aqueous-organic media, the nonaqueous component of which are alcohols, ethers, and acetonitrile were studied. It was shown that, with increasing fraction of water in the solvent, the reaction rate constant grows and the reactivity of N-alkyl anilines depends not only on the structure of the alkyl radical, but also on the content of water in the solvent. It was found that dimethyl sulfoxide has a catalytic effect on these processes. The strategy of choosing the medium in syntheses of biologically active sulfonyl derivatives of fatty-aromatic amines is discussed. A conclusion about the applicability of aqueous-organic media in the production technology of N-alkylated anilines is based on a calculation of the yield of their arenesulfonylation products.

Journal

Russian Journal of Applied ChemistrySpringer Journals

Published: Dec 30, 2014

References

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