N-Chlorosuccinimide-mediated oxidative chlorination of thiols to Nα-protected amino alkyl sulfonyl azides and their utility in the synthesis of sulfonyl triazole acids.

An efficient oxidative chlorination of thiols to Nα-protected amino alkyl sulfonyl azides is delineated. The reaction involves in situ generation of sulfonyl chloride employing N-chlorosuccinimide and tetrabutylammonium chloride-water in acetonitrile, followed by the reaction with sodium azide. The protocol is simple, straight forward, mild and high yielding.