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Synthesis of 3‐(2‐benzothiazolylthio)propanenitrile and related products
Author(s) -
D'Amico John J.,
Suba Lydia,
Ruminski Peter G.
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230605
Subject(s) - chemistry , thionyl chloride , acrylonitrile , acrylamide , organic chemistry , phosphorus , sodium , nuclear chemistry , medicinal chemistry , chloride , polymer , monomer , copolymer
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.