Patent GB-596380-A (GB)
Title: Manufacture of acylated p-aminobenzene sulphonamides
IPC: C07C311/45
Filed: 1944-11-06
Abstract: Acylated p-aminobenzene sulphonamides of the general formula <FORM:0596380/IV/1> wherein R1 and R2 represent hydrogen, or similar or different alkyl, cycloalkyl, aralkyl or aryl residues, R3 is an alkyl, cyclo-alkyl, aralkyl, aryl or heterocyclic residue and Z is a sulphur or oxygen atom, are obtained by the reaction of sulphonamides of the benzene series which carry in the p position to the sulphonamide group a nitrogen containing group; with carboxylic acids of the general formula <FORM:0596380/IV/2> and if necessary converting the p nitrogen containing group into an amino group. Suitable sulphonamides as starting materials are those mentioned in Specification 547,966, and also the urethanes. The above products are also prepared by the action of a -halogen carboxylic acid derivatives or a -sulphonic acid estercarboxylic acid derivatives on the sulphonamides and subsequent reaction with alcohols, phenols, mercaptans or their salts.  A modified method of carrying out the process consists in condensing benzene sulphonhalides, which contain in the p position a nitrogen containing group with salts of amides of the formula <FORM:0596380/IV/3> Numerous examples of suitable alkoxy-, cycloalkoxy-, aralkoxy- and aroxy carboxylic acids as well as corresponding mercapto-carboxylic acids are given.  In examples: (1) 4-aminobenzenesulphon (a 1-ethoxybutyroyl)-amide is prepared by the action of a -ethoxybutyric acid chloride on p - nitrobenzenesulphonamide followed by reduction of the nitro groups; 4-aminobenzenesulphon-(a 1-butoxypropionyl)-amide, the corresponding isobutoxy compound and several other butyroyl-amides are prepared in an analogous manner; (2) 4-aminobenzenesulphon - (a 1 - propylmercaptopropionyl) - amide is prepared by the action of a -propylmercaptopropionic acid chloride on p-nitrobenzenesulphonamide, followed by reduction; (3) 4-aminobenzenesulphon - (cyclopentyloxyacet) - amide is prepared by the action of cyclopentyloxyacetic acid on p-acetylaminobenzenesulphonamide, followed by hydrolysis of the acetyl group; (4) 4-aminobenzenesulphon - (a  - phen - oxyisovaleroyl)-amide is prepared by the action of sodium phenolate on 4-nitrobenzenesulphon-(a -bromoisovaleroyl)-amide followed by reduction; (5) 4-aminobenzenesulphon-(41-chlor-21 -methoxybenzylmercaptoacet)-amide is prepared by the action of 4-chlor-2-methoxybenzylmercaptan on 4-nitrobenzenesulphonchloracetamide followed by reduction; (6) 4-aminobenzenesulphon - (8 - quinolyl - oxyacet) - amide is prepared by the action of 8-quinolyl-oxyacetylchloride on sodium-p-nitrobenzenesulphonamide followed by reduction; (7) 4-aminobenzenesulphon - (a 1 - cinnamyl - oxypropionyl) - amide is prepared by the action of a -cinnamyl-oxypropionylchloride on 4-carbethoxy-aminobenzenesulphonamide followed by hydrolysis of the carbethoxy group.  Samples have been furnished under Sect. 2 (5) according to the following schedules: (1) p-nitrobenzenesulphochloride is treated with a -n-propoxypropionamide giving N1-(a -n-propoxypropionyl) - p - nitrobenzenesulphonamide which is reduced to the corresponding amino compound; (2) p-nitrobenzenesulphochloride is treated with a -n-butoxy-butyramide giving N1-(a -n-butoxy-butyroyl)-p-nitrobenzenesulphonamide which is reduced to the amino compound; and (3) p-acetoamino-benzenesulphochloride is treated with a -n-propoxy-butyramide giving N1 - (a  - n - propoxy - butyrol) - p - acetoamino - benzenesulphonamide which is then hydrolysed to remove the acetyl group.