GB540651A - - Google Patents

Abstract

540,651. Triazines. GEIGY AKT.-GES., J. R. April 24, 1940, No. 7380. Convention date, April 25, 1939. [Classes 2 (iii) and 15 (ii)] Derivatives of 2:4-diamino-1:3:5-triazine or a tantomer thereof, i.e. 2-amino-4-imino-dihydro- 1:3:5-triazine or 2:4-diimino-tetrahydro-1:3:5- triazine are made by re-acting biguanide or a derivative thereof with a carboxylic acid halide in the presence of a non-caustic alkali. Derivatives of biguanide which may be used include compounds of the general formula NH 2 -C(NH)-NH-C(NH)-NHR, where R is an alkyl, aralkyl, or a homocyclic or heterocyclic residue. The carboxylic halides used are preferably the chlorides of acids of high molecular weight, such as saturated and unsaturated higher fatty acids, hydroaromatic acids, resin acids or naphthenic acids. The products, if they contain aryl groups, can be sulphonated, or sulphuric acid residues may be introduced by treating oxyalkyl derivatives with sulphuric or chlorosulphonic acid, or by treating chloralkyl derivatives with sulphates. The products may also be alkylated at the nitrogen atom, to introduce alkyl, oxyalkyl, halogenalkyl, or aminoalkyl groups, and then converted to quaternary ammonium compounds by treating with alkyl halides, dialkyl sulphates or ethylene or other alkylene oxides. The products are intermediates for the production of medicaments and dyestuffs ; they are also useful as textile assistants, for example in vat dyeing. In examples : (1) phenylbiguanide is re-acted with lauryl chloride in toluene in the presence of sodium carbonate to yield 2:4-diimino-5-phenyl- 6-undecyltetrahydro-1:3:5-triazine; the phenylbiguanide may be replaced by methyl-, butyl-, chlorophenyl-, o- or p-toluyl-, anisidyl-, cyclohexyl- and pyridyl-biguanides, or by nitroaryl- or aminoamyl-biguanides, or by amino- and alkylamino-alkyl-biguamides, e.g. diethylaminoethylbiguanide, and the lauryl chloride may be replaced by the chlorides of palm nut fatty acids, or of the fatty acids of blubber or of other fatty acids of naturally occurring fats, oil's and waxes ; (2) phenylbiguanide is similarly re-acted with stearic acid chloride to yield the 5-phenyl- 6-heptadecyl derivative, or with oleic or naphthenic acid chlorides to yield the heptadecenyl or naphthenyl derivatives ; (3) the first-named product of example 2 is sulphonated with oleum ; (4) the first-named product of example 2 is alkylated with dimethyl sulphate and then converted into a quaternary ammonium derivative by further treatment with dimethyl sulphate, or with ethylene oxide or epichlorhydrin ; (5) the product of example 1 is methylated by treatment with dimethyl sulphate ; and (6) phenylbiguanide is re-acted with fencholic acid chloride in toluene in the presence of sodium carbonate and methylated with dimethyl sulphate without isolating the intermediate product; instead of fencholic acid chloride, the bromide or a halide of another acid, e.g. acetic, butyric, valeric, caproic, caprylic or palmitic acid may be used.