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

Zhanhui Yang, 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, Email:

Z. Yang, J. Xu, Synthesis, 2013, 45, 1675-1682.

DOI: 10.1055/s-0033-1338743 (free Supporting Information)


Structurally diverse sulfonyl chlorides were synthesized via N-chlorosuccinimide chlorosulfonation in good yields from S-alkylisothiourea salts, which can be easily prepared from readily accessible alkyl halides or mesylates and inexpensive thiourea. In large-scale syntheses, the water-soluble byproduct succinimide can be conveniently converted into the starting reagent N-chlorosuccinimide with sodium hypochlorite.

see article for more examples

Clean and Economic Synthesis of Alkanesulfonyl Chlorides from S-Alkyl Isothiourea Salts via Bleach Oxidative Chlorosulfonation

Z. Yang, B. Zhou, J. Xu, Synthesis, 2014, 46, 225-229.

Simple Synthesis of Sulfonyl Chlorides from Thiol Precursors and Derivatives by NaClO2-Mediated Oxidative Chlorosulfonation

Z. Yang, Y. Zheng, J. Xu, Synlett, 2013, 24, 2165-2169.

Key Words

sulfonyl chlorides, S-alkyl isothioureas, N-chlorosuccinimide, chlorosulfonation, synthesis

ID: J66-Y2013