Mechanism of formation of benzothiazole-2-thiol

The formation of benzothiazole‐2‐thiol from aniline, carbon disulphide and sulphur at 230°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 pheny...

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Bibliographic Details
Published inJournal of physical organic chemistry Vol. 11; no. 1; pp. 1 - 9
Main Authors Isaacs, Neil S., Ismail, Fyaz, Hilton, Mark J., Coulson, Mark
Format Journal Article
LanguageEnglish
Published Chichester, UK John Wiley & Sons, Ltd 01.01.1998
Subjects
benzothiazole-2-thiol
formation mechanism
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Summary:The formation of benzothiazole‐2‐thiol from aniline, carbon disulphide and sulphur at 230°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 H2S. Mechanisms for the formation of minor byproducts are also considered. © 1998 John Wiley & Sons, Ltd.
Bibliography:ArticleID:POC964
Monsanto
ark:/67375/WNG-NG7WFBL0-V
istex:CE29804CEAE51DF40D7A925A48E5CED3EBEE7A67
ISSN:0894-3230
1099-1395
DOI:10.1002/(SICI)1099-1395(199801)11:1<1::AID-POC964>3.0.CO;2-#