Patent GB-533495-A (GB)
Title: Manufacture of new benzenesulphonamido-derivatives
IPC: C07D277/52
Filed: 1939-01-30
Abstract: 533,495. Sulphonamide compounds. SOC. OF CHEMICAL INDUSTRY IN BASLE. Jan. 30, 1939, Nos. 3109, 3110, 3111 and 3112. Convention dates, Jan. 31, 1938, Sept. 16; 1938, Nov. 24, 1938 and Dec. 22, 1938. [Class 2 (iii)] Benzene-sulphonamide-thiazole compounds containing in the p-position an amino group or a substituent convertible into an amino group are prepared by the methods known for the production of the corresponding compounds in which the thiazole residue is replaced by a hydrocarbon radicle. The convertible substituents consist of an acylamino, nitro, nitroso, azo or hydrazo group or a halogen atom. Thus, a benzene-sulphonic acid halide or ester, appropriately substituted, may be reacted with an aminothiazole; or the corresponding benzene-sulphonamide may be treated with a halogenthiazole. When the p-substituent is one convertible into an amino group it may be so converted ; if an amino group is present, it may be substituted and comprise, for example, an alkylamino, N-acyl-N-alkylamino or aralkylamino group. The benzene-sulphonic acid derivative may contain other substituents such as an alkyl group, whilst the amino thiazoles may be replaced by aminoalkylthiazoles. The products possess therapeutic properties. According to the example, 2-(p-aminobenzenesulphonamido)-thiazole is prepared by (1) heating acetylsulphanilic acid chloride, made from acetanilide and chlorosulphonic acid, with 2-aminothiazole in aqueous solution and treating the resulting (bis-p-acetaminobenzenesulpho)-2-aminothiazole with caustic soda solution ; (2) heating p-acetaminobenzene-sulphonamide with 2-bromthiazole in the presence of potassium carbonate and copper powder, and hydrolyzing the resulting 2-(p-acetaminobenzenesulphonamido)-thiazole. In a manner analogous to (1) is prepared 2-(p-aminobenzenesulphonamido) - 4 - methylthiazole via (bis - p - acetaminobenzenesulpho) - 2 - amino - 4 - methylthiazole. The Specification as open to inspection under Sect. 91 also describes the preparation of compounds containing any heterocyclic nucleus in place of the thiazole residue, by the use of the amino- or halogen-substituted heterocyclic compounds. Of the latter are specified 1-, 2- and 3-aminopyridines, alkylaminopyridines, arylaminopyridines, arylalkylaminopyridines, diaminopyridines, nitroaminopyridines, aminopyridinecarboxylic acids, aminoquinolines, amino-isoquinolines, aminoacridines, amino-oxazoles, halogenpyridines such as 1-bromo-, 3-chloro- and 3 : 5-dibromopyridines, and 2-bromquinoline. It also includes two examples, according to which (1) acetylsulphanilic acid chloride is reacted in cold aqueous potassium hydroxide solution with 2-aminopyridine and the resulting 2- (p - acetaminobenzenesulphonamido) - pyridine then hydrolyzed with caustic soda to split off the acetyl group ; in like manner are prepared 2 - (p - aminobenzenesulphonamido) - 6 - aminopyridine its acetyl derivative, and 2-[p-(p<SP>1</SP>- benzenesulphonamido) - benzenesulphonamido]- pyridine ; (2) acetylsulphanilic acid chloride is stirred into a cold aqueous solution of 3- aminopyridine and the resulting 3-(p-acetaminobenzenesulphonamido) - pyridine hydrolyzed with caustic soda ; 4-(p-aminobenzenesulphonamido)-pyridine and its acetyl derivative are similarly prepared. This subjectmatter does not appear in the Specification as accepted.