Abstract
The addition of amine hydrochlorides to cyanamides is a standard method for the synthesis of substituted guanidines. I It was reported 2 that hydrochlorides of heterocyclic amines can be used in this reaction, and, e.g., heating (180 *C) of 3-amino-l ,2-benzoisothiazole hydrochlorides with an excess ofdimethyicyanamide (1) results in the formation of N,N-dimethyl-N'-(l ,2-benzoisot hiazolyl)guanidine. 3 We have unexpectedly found that the reaction of cyanamide 1 with 2-aminobenzothiazole hydrochlorides (2a) (or its 6-bromo-derivative 2b) under similar conditions is a more complicated process, viz., the condensation of two eyanamide molecules with two molecules of aminoazole hydrochloride (with the elimination of the dimethylamine hydrochloride and NH4CI). This results in previously unknown derivatives of 4-(benzothiazol2 y l ) i m i n o 2 d i m e t h y l a m i n o 4 H i , 3 , 5 t r i a z i n o [2,I-blbenzothiazole (3a,h) isolated in moderate yields.
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