41526-42-5Relevant academic research and scientific papers
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.
A NEW ROUTE TO 2H-(1,2,4)TRIAZINO(3,4b)BENZOTHIAZOLE-3(4H)-ONE (4)
D'Amico, John J.,Bollinger, Frederic G.,Dahl, William E.
, p. 71 - 76 (2007/10/02)
The reaction of 3-(carbethoxymethyl)benzothiazoline-2-thione (1) with excess hydrazine in an aqueous medium at 25-30 deg or 95-100 deg C afforded the hydrazide (3) in 99percent yield and the titled heterocyclic compound (4) in 63percent yield, respectively.Under the same reaction conditions and replacing the above electrophile with 3-(carbethoxymethyl)-2-benzothiazoline furnished the hydrazide (5) in 45percent yield and a 6percent yield of 5 plus a high yield of a resinous mixture, respectively.Possible mechanism and supporting NMR and mass spectral data are discussed.
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.
