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Synthesis of 2‐thioxo‐3‐benzothiazolineacetonitrile and related products
Author(s) -
D'Amico John J.,
Suba Lydia,
Ruminski Peter G.
Publication year - 1985
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.5570220603
Subject(s) - chemistry , yield (engineering) , dimethylformamide , acetone , electrophile , sulfide , solvent , organic chemistry , cyanide , medicinal chemistry , sodium sulfide , potassium cyanide , potassium , catalysis , materials science , metallurgy
Attempts to thermally rearrange 2‐benzothiazolylthioacetonitrile ( 1) to the titled compound 8 failed. The reaction of 3‐chloromethyl‐2‐benzothiazolinethione with potassium cyanide in dimethylformamide (DMF) or dimethylsulfoxide (DMSO) at 25‐30° afforded 8 in 98% yield. Whereas replacing the DMF or DMSO solvent with acetone furnished the unexpected sulfide 9 in 92% yield. Substituting 3‐chloromethyl‐2‐benzoxazoline‐thione as the electrophile in the same reaction gave the sulfide 10 in 95% yield. Possible mechanisms and supporting nmr data are discussed.