Synthesis of sulfonimidamides from sulfinamides by oxidation with N-chlorosuccinimide

BACKGROUND: The synthesis of sulfonimidamides involves the nucleophilic substitution of a sulfonimidoyl chloride with an amine. However, only four chlorinating systems have been reported for the preparation of the sulfonimidoyl chloride intermediates. Whereas some of them have shown a rather limited substrate spectrum, the most versatile and commonly used tert-butyl hypochlorite is known to be explosive. To establish alternative methods for the synthesis of these molecules is therefore desirable. RESULTS: The preparation of various p-tolylsulfonimidamides through the reaction of the corresponding N-protected p-tolylsulfinamides and a number of amines in the presence of N-chlorosuccinimide was achieved at room temperature in 50–97% yield. CONCLUSION: A convenient alternative procedure for the synthesis of sulfonimidamides from sulfinamides and various amines and sulfonamides using N-chlorosuccinimide as halogenating agent has been developed.