GB552887A - Sulphonamide derivatives - Google Patents

Abstract

552,887. Sulphonamido compounds. HAWORTH, E., ROSE, F. L., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. July 25, 1941, No. 9458. [Class 2 (iii)] Sulphonamido-pyrimidines are prepared by reacting a benzenesulphonamido-guanidine having an amino, acylamino or nitro group in the p-position with a #-dicarbonyl compound containing the grouping -CO-CHR-CO- wherein R represents hydrogen or a hydrocarbon radicle. The products are useful therapeutically or for the manufacture of therapeutic compounds. The #-dicarbonyl compounds may be #-diketones, #-ketocarboxylic esters and malonic esters, e.g. acetylacetone, methylacetylacetone, propionylacetone, n-butyrylacetone, dipropionylmethane, hexanoylacetone, heptanoylacetone, dodecanoylacetone, ethyl acetoacetate, ethyl propionylacetate, ethyl benzoylacetate, dimethyl malonate, dipropyl malonate, ethyl oxaloacetate and the ethyl ester of oxalacetone. Examples are given of the preparation of (1) 2-(4<SP>1</SP>-nitrobenzenesulphonamido)-4-methyl-6-hydroxypyrimidine from 4-nitrobenzenesulphonylguanidine and ethyl acetoacetate ; the 41-acetylamino product is similarly prepared ; (2) 2-(4'-nitrobenzenesulphonamido)-4:6-dimethylpyrimidine from 4-nitrobenzenesulphonylguanidine and acetylacetone ; the 4<SP>1</SP>-amino product is similarly prepared from sulphanilylguanidine, and the 4:5:6-trimethyl product using methylacetylacetone ; (3) 2-(4<SP>1</SP>-aminobenzenesulphonamido) - 4 - hydroxy - 6 - carbethoxypyrimidine from sulphanilylguanidine and ethyl oxaloacetate ; (4) 2 - (41 - nitrobenzenesulphonamido) - 4 - methyl 6 - carbethoxypyrimidine from 4 - nitrobenzenesulphonylguanidine and the ethyl ester of oxalacetone ; (5) 2-(4'-nitrobenzenesulphonamido)-4:6-dihydroxypyrimidine from 4-nitrobenzenesulphonylguanidine and diethyl malonate. Dodecanoylacetone is obtained by condensing methyl undecyl ketone with ethyl acetate.