Synthesis of 2‐thioxo‐3‐benzothiazolineacetonitrile and related products

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

Research output: Contribution to journalArticlepeer-review

13 Scopus citations


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.

Original languageEnglish
Pages (from-to)1479-1482
Number of pages4
JournalJournal of Heterocyclic Chemistry
Issue number6
StatePublished - 1985


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