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Water-promoted chlorination of 2-mercaptobenzothiazoles

Wimmer , Laurin and Parmentier, Michael and Riss, Bernard and Kapferer, Tobias and Ye, Chao and Li, Lei and Kim, Hongyong and Li, Jialiang (2018) Water-promoted chlorination of 2-mercaptobenzothiazoles. Synthesis.

Abstract

Substituted benzothiazoles play an important role in medicinal
chemistry due to their pharmacological properties. Their 2-substituted
derivatives are often prepared from 2-chlorobenzothiazoles, which in turn can
be made from the 2-mercapto precursor using sulfuryl chloride. In practice,
this seemingly straightforward, and widely used reaction can be impeded by
poor reproducibility and reaction yields. In this communication we report the
importance of acid as catalyst for the parent reaction. The addition of water to
the reaction mixture represents a facile and practical method for generating
acid in situ. This simple solution reproducibly ensured excellent yields of a
variety of chlorinated products.

Item Type: Article
Keywords: 2-chlorobenzothiazole, sulfuryl chloride, chlorination, acid catalyzed, water-promoted
Date Deposited: 12 Apr 2018 00:45
Last Modified: 12 Apr 2018 00:45
URI: https://oak.novartis.com/id/eprint/34666

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