A Practical Synthesis of N-Substituted 1,2-Benzisothiazolin-3-ones from N,N′-Disubstituted 2,2′-Dithiodibenzamides

 

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Abstract

A variety of N-substituted 1,2-benzisothiazolin-3-ones were easily synthesized from N,N′-disubstituted 2,2′-dithiodibenz­amides in the presence of O-methylhydroxylamine hydrochloride. Derivatives with a primary, secondary, or tertiary alkyl group or an aryl group on the N-1 nitrogen of the 1,2-benzisothiazolin-3-one were obtained.

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The stoichiometry of the reaction means that 100% yield corresponds to 2 equiv of 2 produced for 1 equiv of 1.