Synthesis and Properties of sym-Triazine Derivatives. 18. Synthesis of N-Substituted 2,4-Diamino-6-(benzothiazolyl-2-thiomethyl)-sym-triazines

The condensation of methyl benzothiazolyl-2-thioacetate with N-substituted biguanides in the presence of sodium methylate gave 2-amino-4-(RR'-amino)-6-(benzothiazolyl-2-thiomethyl)-sym-triazines. In a number of cases the 1,1-disubstituted 5-(benzothiazolyl-2-thioacetyl)biguanides could also be separated and these could be cyclized by refluxing in DMF to the corresponding substituted sym-triazines described. The latter type of compound was also synthesized by treating 2-amino-4-trichloromethyl-6-(benzothiazolyl-2-thiomethyl)-sym-triazine with primary and secondary aliphatic and heterocyclic amines or by the reaction of N-substituted 2,4-diamino-6-chloromethyl-sym-triazines with 2-mercaptobenzothiazole.