Patent GB-666475-A (GB)
Title: Preparations for use in antibacterial therapy
IPC: H01K9/04
Filed: 1947-08-27
Abstract: p-Benzylsulphonamido-benzoic acid is prepared by adding benzyl sulphonyl chloride in small portions with cooling to a solution of ethyl p-amino benzoate in pyridine, the resulting ethyl ester being hydrolysed by aqueous NaOH.  Using other appropriate sulphonyl chlorides, the m-benzyl-, p-phenethyl-, and p-heptyl-sulphonamido benzoic acids can be obtained.  The Specification as open to inspection under Sect. 91 comprises also the following:- 4-Hydroxy-41-carboxybenzenesulphonanilide is prepared by adding an aqueous solution of sodium nitrite to a slurry of p-sulphanilamido benzoic acid and crushed ice and adding the resulting suspension to a boiling solution of aqueous sulphuric acid. N-benzyl-4-cyanobenzenesulphonamide is prepared by adding portions of 4-cyanobenzenesulphonyl chloride to a solution of benzylamine in dry pyridine.  p-Carboxyphenyl-sulphonamido-phenylmethane is prepared by refluxing an alcoholic solution of N - benzyl - 4 - cyanobenzene - sulphonamide while passing dry hydrogen chloride therethrough, removing the alcohol and hydrolysing the resulting N-benzyl-4-carbonylbenzene-sulphonamide by refluxing with aqueous caustic soda.  2-Benzylsulphonamido-4-carboxy-thiazol is prepared by adding portions of benzene-sulphonyl chloride to a solution of 2-amino-4-carboxythiazole in pyridine 1-p-Carboxyphenyl-sulphonamido-n-pentane is prepared by reacting 4-carboxybenzene-sulphonyl chloride with n-amylamine in a chilled solution in acetone.  p - (m - Nitrobenzenesulphonamido) - benzoic acid is prepared by adding m-nitrobenzenesulphonyl chloride slowly to a solution of p-aminobenzoic acid in pyridine. 3-Amino-41-carboxybenzenesulphonanilide is prepared by suspending p-(m-nitrobenzenesulphonamido)-benzoic acid in dry alcohol containing hydrogen chloride and reducing the suspension by means of hydrogen in the presence of a palladium-charcoal catalyst.  Ethyl p-(o-nitrobenzenesulphonamido)-benzoate is prepared by adding o-nitrobenzene sulphonyl chloride to a solution of ethyl p-aminobenzoate in pyridine.  2-Amino-41-carboxybenzenesulphonanilide is prepared by hydrolysing ethyl - p - (o - nitrobenzenesulphonamido) - benzoate in aqueous caustic soda and reducing the resulting acid with hydrogen in a dioxane-water mixture using a palladium-charcoal catalyst.  N-sulphanilyl-N-methyl-p-carboxyaniline is prepared by condensing acetyl-aminobenzenesulphonyl chloride with p-methyl amino benzoic acid in dilute sodium hydroxide solution and subjecting the resulting acetyl compound to alkaline hydrolysis.  N - (p - nitrobenzyl) - 4 - carboxybenzene - sulphonylamide is prepared by adding portions of 4-carboxybenzene sulphonyl chloride to a solution of p-nitrobenzylamine in acetone.  p - Carboxyphenylsulphonamido - p - aminophenyl-methane is prepared by dissolving N-(p-nitro - benzyl) - 4 - carboxybenzene - sulphonylamide in a mixture of " Cellosolve " (Registered Trade Mark) and isopropyl alcohol containing hydrogen chloride and reducing the solution with hydrogen in the presence of a palladium charcoal catalyst.  Ethyl - p - (m - nitrobenzylsulphonamido) - benzoate is prepared by adding portions of m-nitrobenzylsulphonyl chloride to a solution of ethyl p-aminobenzoate in pyridine.  p-(m-Aminobenzylsulphonamido)-benzoic acid is prepared by hydrogenating a suspension of ethyl - p - (m - nitrobenzyl - sulphonamido) - benzoate in methyl cellulose in the presence of a palladium-charcoal catalyst and hydrolysing the resulting ester with caustic soda solution. p-Aminophenyl-p-carboxyphenyl sulphone is prepared by adding portions of chromic oxide in glacial acetic acid to a hot solution of p-nitrophenyl p-tolylsulphone in glacial acetic acid and reducing a methyl cellosolve solution of the resulting nitro compound by hydrogen in the presence of a palladium-charcoal catalyst. p-Aminobenz-o-carboxyphenyl-amide is prepared by adding an acetone solution of p-nitrobenzoyl chloride to a solution of anthranilic acid in aqueous sodium hydroxide, and hydrogenating the resulting o-(p-nitrobenzamido)-benzoic acid in the presence of a palladium-charcoal catalyst.  N-p-carboxyphenyl-phenylacetamide is prepared by slowly adding phenylacetyl chloride to a solution of p-aminobenzoic acid in acetone.  p-Carboxyphenyl-a -tolylamine is prepared by refluxing a mixture of p-aminobenzoic acid, benzylchloride, potassium carbonate and water, and acidifying the product.  This subject-matter does not appear in the Specification as accepted.