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

D'Amico John J. | Zendy; Suba Lydia | Zendy; Ruminski Peter G. | Zendy

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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.

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