Synthesis of 3‐(2‐benzothiazolylthio)propanenitrile and related products

John J. D'Amico, Lydia Suba, Peter G. Ruminski

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5 Scopus citations


The reaction of 2‐mercaptobenzothiazole, 2‐mercaptobenzoxazole or 5‐chloro‐2‐mercaptobenzothiazole with either acrylonitrile or acrylamide under basic conditions afforded the N‐cyanoethylated products 1, 2 and 3 or the N‐amidoethylated products 4, 5 and 6, respectively. The reaction of the sodium salts of the same thiazolethiols with 3‐chloropropionitrile furnished a mixture containing the N‐cyanoethylated products 1, 2 and 3 and the unknown S‐cyanoethylated products 7, 8 and 9, respectively. Whereas, substituting 3‐chloropropionamide for 3‐ chloropropionitrile in the same reaction gave only the S‐substituted products 10, 11, and 12, respectively. The treatment of 10, 11 or 12 with phosphorus oxychloride or thionyl chloride in DMF afforded 7, 8 and 9 in excellent yields. Possible mechanisms and supporting nmr data are discussed.

Original languageEnglish
Pages (from-to)1629-1635
Number of pages7
JournalJournal of Heterocyclic Chemistry
Issue number6
StatePublished - 1986


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