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Synthesis of sulfonimidamides from sulfinamides by oxidation with N-chlorosuccinimide.

ABSTRACT:

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.

SUBMITTER: Mancheno OG

PROVIDER: S-EPMC2151070 | biostudies-literature | 2007 Sep

REPOSITORIES: biostudies-literature

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Synthesis of sulfonimidamides from sulfinamides by oxidation with N-chlorosuccinimide.

Mancheño Olga García OG Bolm Carsten C

Beilstein journal of organic chemistry 20070925

<h4>Background</h4>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 de ...[more]

PMID: 17894869

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