GB557985A - Improvements in or relating to water soluble sulphonamides - Google Patents

Abstract

557,985. Water soluble sulphonamide compounds. BRITISH SCHERING RESEARCH LABORATORIES, Ltd., HEY, D. H., and BEYNON, J. H. June 10, 1942, No. 7958. [Class 2 (iii)] Water soluble sulphonamide compounds of the general formula p-XNH.C 6 H 4 .SO 2 .NH-acyl where X=-CH 2 SO 3 H, -CHRSO 3 H (R being alkyl aryl or aralkyl), -CH 2 SO 2 H, COOH (CH 2 ) n CO-, or the residue of a sugar, are prepared by treating a p-aminobenzenesulphonacylamide with (1) an aldehyde bisulphite addition compound, (2) sodium formaldehyde sulphoxylate, (3) an anhydride of a dibasic acid, or (4) a sugar. Alternatively, a compound XNH.C 6 H 4 -SO 2 .NH 2 (where X has the significance defined above), with an acylating agent. The acidic hydrogen in the group X as well as in the acylamido group may be replaced by a metal. In examples (1) sodium aminobenzene-sulphonacetamide is added to the addition compound of acetaldehyde with sodium metabisulphite to give disodium aminobenzenesulphonacetamide-N<SP>4</SP>-ethyl - #-sulphonate. (2) As in example (1) using aminobenzenesulphonacetamide instead of its sodium salt with the formation of the corresponding mono-sodium compound. (3) Sodium aminobenzenesulphonacetamide is added to an aqueous solution of benzaldehyde and sodium metabisulphite to form disodium aminobenzenesulphonacetamide-N<SP>4</SP>-benzyl- #-sulphonate. (4) As in example (3) using the mono-sodium compounds as in example (2). (5) Sodium aminobenzenesulphonacetamide is added to a mixture of formaldehyde and sodium metabisulphite to form disodium aminobenzenesulphonacetamide - N<SP>4</SP> - methyl - # - sulphonate. (6) As in example (5) using the monosodium compound as in example (2). (7) Succinic anhydride is added to a solution of aminobenzenesulphonacetamide in dioxane to give N<SP>4</SP>-#-carboxypropionylaminobenzenesulphonacetamide. (8) A mixture of aminobenzenesulphonacetamide and sodium formaldehyde sulphoxylate is added to glacial acetic acid to form disodium aminobenzenesulphonacetamide - N<SP>4</SP> - methylenesulphinate. (9) Aminobenzenesulphonacetamide is added to an aqueous solution of sodium formaldehyde sulphoxylate to form aminobenzenesulphonacetamide - N<SP>4</SP> - methylenesulphinate. (10) Aminobenzenesulphonacetamide and α- glucose are refluxed in alcohol solution containing ammonium chloride to. form the N<SP>4</SP>-α- glucoside of aminobenzenesulphonacetamide. Specifications 462,765, 470,462, 487,378, 500,674, 502,558, 503,271, 524,011 and 541,958 are referred to.