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Mechanism of formation of benzothiazole-2-thiol

✍ Scribed by Neil S. Isaacs; Fyaz Ismail; Mark J. Hilton; Mark Coulson

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
232 KB
Volume
11
Category
Article
ISSN
0894-3230

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✦ Synopsis

The formation of benzothiazole-2-thiol from aniline, carbon disulphide and sulphur at 230Β°C was shown to occur by a sequence of three principal steps. Labelling experiments confirmed that both sulphur atoms originate from carbon disulphide. An initial polar reaction to form thiocarbanilide via phenylcarbamic acid and a tetrahedral intermediate is followed by radical cyclization of these to benzothiazole-2-thiol and 2-phenylaminobenzothiazole; the latter is converted into the desired product by a polar displacement of aniline by H 2 S. Mechanisms for the formation of minor byproducts are also considered.

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