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

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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