GB584585A - Manufacture of derivatives of ªÐ-aminobenzenesulphonylguanidine - Google Patents

Abstract

p-Acylamino-, p-nitro-, or p-amino-benzenesulphonylacylguanidines of the probable general formula <FORM:0584585/IV/1> wherein R represents -NH Acyl, -NO2 or -NH2 and R1 represents alkyl or aryl, are obtained by: (a) direct diacylation of p-aminobenzenesulphonylguanidine; (b) direct monoacylation of a p-acylaminobenzenesulphonyl-, p-aminobenzenesulphonylacyl-, p-nitrobenzenesulphonylacyl-, or p - nitrobenzenesulphonyl - guanidine; (c) the action of ammonia urea or ammonium carbonate on a p-acylaminobenzene-sulphonylacylmethylisothiourea; (d) condensing a p-acylaminobenzenesulphonylhalide-, or (e) a p-nitrobenzenesulphonylhalide-, with an acylguanidine or salt thereof; (f) reducing a p-nitrobenzenesulphonylacylguanidine to the corresponding p - amino compound. In examples: (1) p-aminobenzenesulphonylguanidine is boiled with acetic anhydride and pyridine to obtain p - acetylaminobenzenesulphonylacetyl - guanidine, which is similarly obtained by using as starting-materials either p-acetylaminobenzenesulphonyl-, or p - aminobenzenesulphonylacetyl-guanidine, pyridine being optional; (2) p-aminobenzenesulphonylguanidine is treated with propionic anhydride and pyridine, or p - propionylaminobenzenesulphonylguanidine with propionic anhydride to obtain the corresponding diacyl compound; (3) p-acetylaminobenzenesulphonylacetylmethylisothiourea is treated with ammonia to obtain p-acetylaminobenzenesulphonylacetylguanidine; (4) p-acetylaminobenzenesulphonyl chloride is heated with acetylguanidine and pyridine to obtain p-acetylaminobenzenesulphonylacetylguanidine; (5) p - acetylaminobenzenesulphonylguanidine is treated with propionic anhydride and pyridine to obtain p-acetylaminobenzenesulphonylpropionylguanidine; (6) p-nitrobenzenesulphonyl chloride and acetyl guanidine are together treated with pyridine to obtain p-nitrobenzenesulphonylacetylguanidine; (7) acetylguanidine acetate, in pyridine, is heated with p-nitrobenzenesulphonyl chloride to obtain p-nitrobenzenesulphonylacetylguanidine; (8) p-nitrobenzenesulphonylguanidine is heated under reflux with acetic anhydride and pyridine to obtain p-nitrobenzenesulphonylacetylguanidine; (9) p-nitrobenzenesulphonylacetylguanidine is hydrogenated at room temperature to obtain the corresponding p-amino compound; (10) p-nitrobenzenesulphonylguanidine and benzoicanhydride are heated to obtain crude p-nitrobenzenesulphonylbenzoylguanidine, which is hydrogenated as in (9) to obtain the corresponding p-amino compound. p - Acetylaminobenzenesulphonylacetylmethylisothiourea is obtained by heating p-acetylaminobenzenesulphonylmethylisothiourea with acetic anhydride in presence of anhydrous sodium acetate. p-Nitrobenzenesulphonylguanidine is obtained by condensing p-nitrobenzenesulphonyl chloride with guanidine nitrate in presence of sodium hydroxide.