Convenient and Environment-Friendly Synthesis of Sulfonyl Chlorides from S-Alkylisothiourea Salts via N-Chlorosuccinimide Chlorosulfonation

Zhanhui Yang; Jiaxi Xu

doi:10.1055/s-0033-1338743

Synthesis, Table of Contents

Synthesis 2013; 45(12): 1675-1682
DOI: 10.1055/s-0033-1338743

paper

Convenient and Environment-Friendly Synthesis of Sulfonyl Chlorides from S-Alkylisothiourea Salts via N-Chlorosuccinimide Chlorosulfonation

Zhanhui Yang

State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China Fax: +86(10)64435565 Email: jxxu@mail.buct.edu.cn

,

Jiaxi Xu*

State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China Fax: +86(10)64435565 Email: jxxu@mail.buct.edu.cn

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Abstract

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Abstract

A convenient, practical, and environmentally friendly method for the synthesis of sulfonyl chlorides has been developed. Structurally diverse sulfonyl chlorides were synthesized in moderate to excellent yields from S-alkylisothiourea salts, which can be easily prepared from readily accessible alkyl halides or mesylates and inexpensive thiourea, via N-chlorosuccinimide chlorosulfonation. In large-scale syntheses, the byproduct succinimide from ‘waste water’ can be conveniently converted into the starting reagent N-chlorosuccinimide with sodium hypochlorite (bleach) to make the method sustainable.

Key words

sulfonyl chloride - S-alkylisothioruea - N-chlorosuccinimide - chlorosulfonation - synthesis

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