GB676024A - Process for the production of 2-(halogen-aryl)-amino-4-amino-1,3,5-triazines - Google Patents

Abstract

2-(Halogen-aryl)-amino-4-amino-1 : 3 : 5-triazines are manufactured by subjecting a 1-aryl-or 1-halogen-aryl-biguanide to ring-closing condensation with an excess of formic acid or a salt or other derivative thereof capable of reacting, and, when using the first-named starting materials, subsequently introducing halogen into the aryl group. The products, which possess diuretic properties, yield water-soluble salts with organic or inorganic acids. In examples: (1) 1 - p - chlorophenylbiguanide hydrochloride is reacted with sodium formate, and the resulting formate of the biguanide is boiled with more formic acid to produce 2-(p-chlorophenyl) - amino - 4 - amino - 1 : 3 : 5 - triazine, which may be converted into its hydrochloride; (2) 1-p-bromophenylbiguanide formate similarly yields 2-(p-bromophenyl)-amino-4-amino-1 : 3 : 5-triazine and its hydrochloride; (3) 2 - phenylamino - 4 - amino - 1 : 3 : 5 - triazine hydrochloride is treated with bromine in aqueous solution to give 2-(21 : 41 : 61-tribrom phenyl) - 4 - amino - 1 : 3 : 5 - triazine. The Specification as open to inspection under Sect. 91 comprises also the manufacture of other compounds of the general formula <FORM:0676024/IV (b)/1> (wherein R1 represents a free or substituted aryl group or a heterocyclic group and R2 hydrogen, an alkyl or substituted alkyl group or a free or substituted heterocyclic residue, or R1 and R2 jointly form with the nitrogen atom a heterocyclic ring such as a piperidine ring, and R3 represents hydrogen or a free or substituted alkyl or aryl group), the use, for condensation with substituted guanidines as above, of aliphatic acids other than formic acid (e.g. acetic or propionic acid), or aromatic acids (e.g. benzoic acid) or their functional derivatives (e.g. esters, ortho-esters, amides or amidines), and the following alternative methods of preparation: (a) heating acid amides of the substituted biguanides, alone or in solution; (b) reacting the corresponding substituted dicyandiamides with acid amides. Additional examples describe the preparation of 2-anilino-, 2-(p-dimethylaminoanilino)-, 2-o- and p-toluidino- and 2 - (N - methylanilino) - 4 - amino - 1 : 3 : 5 - triazine by condensing with formic acid the appropriately substituted biguanides (obtained from the corresponding amines and dicyandiamide). Further products specified are 2-anilino-4-amino-6-methyl- and -6-ethyl-1 : 3 : 5-triazine, and 2-(p-methoxy-, p-ethoxy- and 21 : 41 : 51 - trimethyl-phenyl)-amino-4-amino-1 : 3 : 5-triazine. This subject-matter does not appear in the Specification as accepted.