Patent GB-537291-A (GB)
Title: Manufacture of therapeutically useful heterocyclic compounds
IPC: C07D213/76
Filed: 1939-09-14
Abstract: 537,291. Sulphonamido compounds. MAY & BAKER, Ltd., and ASHLEY, J. N. Sept. 14, 1939, Nos. 25812 and 31001. [Class 2 (iii)] Sulphonamido compounds of the formula in which Y is a pyridine, quinoline or thiazole nucleus and Y' is a dialkylaminoalkyl group, are prepared by (1) treating a compound p-NH 2 .C 6 H 4 .SO 2 NHY with a dialkylaminoalkyl halide ; instead of the p-amino group, an acylamino group convertible thereto by hydrolysis may be present, or a nitro or other nitrogen containing group readily reducible to the amino group, or a halogen convertible to the amino group by reaction with ammonia, the subsequent conversion being effected in each case ; (2) condensing a dialkylaminoalkyl derivative of Y.NH  2  with a benzenesulphonyl chloride, ester or anhydride which is substituted in p-position by an above-mentioned group convertible into an amino group, such conversion being subsequently effected; (3) reacting a dialkylaminoalkylamine with a benzenesulphonyl chloride, ester or anhydride substituted in the p-position by a group as above-mentioned convertible into an amino group and then making the conversion. The products are useful therapeutically. According to the examples : (1) 2-p-acetylaminobenzenesulphonamidopyridine is treated with #-diethylaminoethyl chloride and the product hydrolysed to give 2-p-aminobenzenesulphon-(#-diethylaminoethyl) - amidopyridine ; (2) the same compound is also obtained by condensing 2-aminopyridine first with ptoluenesulphochloride and then with #-diethylaminoethyl chloride to yield 2-p-toluenesulphon- (#-diethylaminoethyl)-aminopyridine; hydrolysing to 2-#-diethylaminoethylaminopyridine, treating with acetanilido-p-sulphonyl chloride and again hydrolysing ; (3) the same compound is also prepared by reacting 2-p-nitrobenzenesulphonamidopyridine with #-diethylaminoethyl chloride and reducing with iron and acetic acid; (4) the same compound is further prepared by treating 2-p-chlorbenzenesulphonamidopyridine with #-diethylaminoethyl chloride and heating the product with ammonia in presence of cuprous chloride ; (5) 2-p-aminobenzenesulphon-(#-diethylaminoethyl) - amino - thiazole results when 2-p-acetylaminobenzenesulphonamidothiazole is reacted with #-diethyl. aminoethyl chloride and the product hydrolysed; (6) 4-methyl-2-p-aminobenzenesulphon - (#-diethylaminoethyl)-aminothiazole is obtained by the hydrolysis of the condensation product of 4 - methyl - 2 - p - acetylaminobenzenesulphonamidothiazole with #-diethylaminoethyl chloride ; the 5-methyl compound is similarly prepared; (7) p-acetylaminobenzenesulphon-#- diethylaminoethylamide, prepared by condensing acetylsulphanilamide with #-diethylaminoethyl chloride or p-acetylaminobenzenesulphonyl chloride with #-diethylaminoethylamine, is Heated with 5-nitro-2-bromoquinoline in the presence of copper bronze and the product hydrolysed to give 5-nitro-2-p-amihobenzenesulphon - (#- diethylaminoethyl) - aminoquinoline ; (8) 6-methoxy-8-p-aminobenzenesulphon- (#-diethylaminoethyl)-amidoquinoline is obtained by interacting #-diethylaminoethyl chloride and 6-methoxy-8-p-acetylaminobenzenesulphonamidoquinoline and hydrolysing the product; (9) 2-p-aminobenzenesulphon -(#-diethylaminoethyl)-amidopyridine is prepared by direct treatment of 2-p-aminobenzenesulphonamidopyridine with #-diethylaminoethyl chloride. The first Provisional Specification also refers to the production of compounds in which Y<SP>1</SP> is an aminoalkyl or monoalkylaminoalkyl group.