Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom