Patent GB-610379-A (GB)
Title: Improvements in the manufacture of diguanide compounds
IPC: C07C279/26
Filed: 1946-04-03
Abstract: Organic sulphonic acid salts of diguanides of the general formula R1R2N.C(: NH).NH.C(: NH).NH2.X.SO3H (where R1 and R2 are hydrogen, alkyl, aryl, aralkyl and alicyclic radicals or together form a divalent polymethylene group, and X is a hydrocarbon radical) are made by heating dicyandiamide to 140-180 DEG  C. with an ammonium or primary or secondary mono-amine sulphonic acid salt of the general formula NHR1R2.X.SO3H so as to form a reaction product which consists in preponderating amount of the desired salt.  The reaction is carried out at about 150 DEG  C. using substantially equimolecular proportions of the reacting substances.  In examples: (1) ammonium benzenesulphonate and dicyandiamide are heated to 170 DEG  C. and the diguanide benzenesulphonate formed is converted to diguanide sulphate monohydrate by adding ammoniacal copper sulphate, dissolving the precipitated copper salt of diguanide in sulphuric acid and crystallizing the product from the solution; (2) 1-methyldiguanide benzenesulphonate is made by heating dicyandiamide and methylamine benzenesulphonate to 160 DEG  C. and crystallizing the product from isopropyl alcohol; (3) isopropyldiguanide toluene-p-sulphonate is made by heating dicyandiamide and isopropylamine toluene-p-sulphonate to 160 DEG  C. and crystallizing from isopropyl alcohol; (4) 1-cyclohexyldiguanide is made by heating dicyandiamide and cyclohexylamine toluene-p-sulphonate to 140 DEG  C. and crystallizing from water; (5) 1,1-dimethyldiguanide toluene - p - sulphonate is made by heating dicyandiamide and dimethylamine toluene-p-sulphonate to 160 DEG  C. and crystallizing from isopropyl alcohol; (6) 1,1-diethyldiguanide toluene-p-sulphonate is made by heating dicyandiamide with diethylamine toluene-p-sulphonate at 140 DEG  C., treating with an aqueous ammoniacal solution of copper toluene-p-sulphonate, filtering off the copper diethylguanide which is precipitated, treating with hydrogen sulphide, filtering, evaporating the solution to dryness, and recrystallizing from acetone; (7) 1,1 - pentamethylenediguanide toluene-p-sulphonate is made by heating dicyandiamide and piperidine toluene-p-sulphonate at 140 DEG  C.; (8) 1-benzylguanide toluene-p-sulphonate is made by heating dicyandiamide and benzylamine toluene - p - sulphonate at 140 DEG  F. and worked up through the copper derivative; (9) 1-phenyldiguanide is made by heating dicyandiamide and aniline benzenesulphonate at 160 DEG  C. and then adding sodium hydroxide; (10) 1 - (p - sulphonamidophenyl) - diguanide benzenesulphonate is made by heating dicyandiamide and sulphanilamide benzenesulphonate at 160 DEG  C.; (11) 1-methyl-1-phenyldiguanide is made by heating dicyandiamide and methylaniline benzene sulphonate at 140 DEG  C.; and (12) 1,1-diphenyldiguanide toluene-p-sulphonate is made by heating dicyandiamide and diphenylamine toluene-p-sulphonate at 140 DEG  C.  A sample of 1-phenyldiguanide methanesulphonate has been filed under Sect. 2 (5), prepared from dicyandiamide and aniline methanesulphonate.  Specifications 593,659 and 593,675 are referred to.