41526-42-5Relevant articles and documents
Convenient synthesis of 2-(thiocyanomethylthio)benzothiazole
Muthusubramanian, Lakshmi,Mitra, Rajat B.,Sundara Rao,Raghavan
, p. 1331 - 1334 (2007/10/03)
A highly efficient and general route has been developed for 2-(thiocyanomethylthio)benzothiazole 3 which is synthesised by reacting a chlorinating agent with 2-mercaptobenzothiazole 1 followed by reactions involving 2-(methylthio)benzothiazole 1b and 2-(methylsulfinyl)benzothiazole 2 under various conditions.
Synthesis of 2-Thioxo-3-benzothiazolineacetonitrile and Related Products
D'Amico, John J.,Suba, Lydia,Ruminski, Peter G.
, p. 1479 - 1482 (2007/10/02)
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 deg C afforded 8 in 98percent yield.Whereas replacing the DMF or DMSO solvent with acetone furnished the unexpected sulfide 9 in 92percent yield.Substituting 3-chloromethyl-2-benzoxazolinethione as the electrophile in the same reaction gave the sulfide 10 in 95percent yield.Possible mechanisms and supporting nmr data are discussed.