Patent GB-516288-A (GB)
Title: The manufacture of new heterocyclic compounds
IPC: C07D213/71
Filed: 1938-06-23
Abstract: 516,288. Pyridine sulphonamides. MAY & BAKER, Ltd., EWINS, A. J., PHILLIPS, M. A.; and NEWBERY, G. June 23, 1938, Nos. 18694 and 30010. [Class 2 (iii)] Amino substituted pyridine sulphonamides of the general formula NH2.B.SO2.NR<1>R where B is the pyridine radical, and R<1> and R may be hydrogen or an alkyl, aryl, or aralkyl group and where R is hydrogen R<1> may be a pyridine residue are prepared either (1) by the action of ammonia or alkyl-, aryl-, or aralkyl amines or amino-pyridine on the corresponding sulphonyl chlorides NH2.B.SO2Cl, or (2) by the action of ammonia on compounds of the formula X.B.SO2.NR<1>R, where X is a halogen atom. The sulphonyl chlorides used in alternative (1) above may be prepared by the action of chlorosulphonic acid on either corresponding sulphonic acid or on the amino-pyridine. In the latter case the free sulphonic acid need not be isolated, but the sulphonyl chloride prepared in one operation. In examples (1) 2-amino-pyridine- 5-sulphonic acid is treated with chloro-sulphonic acid, and the product poured on to ice and extracted with chloroform to give 2-aminopyridine-5-sulphonyl chloride. This is then converted by the action of ammonia into 2-amino-pyridine-5-sulphonamide. (2) The 2- amino-pyridine-5-sulphonyl chloride prepared as in example (1) is reacted with 2-amino-pyridine to give 2-(2<1>-amino-pyridine-5<1>-sulphonamido) pyridine. (3) 2-chloropyridine-5-sulphonamide is treated with ammonia in the presence of cuprous chloride to give 2-amino-pyridine-5- sulphonamide. (4) 2-amino-pyridine is reacted with 2-chloro-pyridine-5-sulphonchloride in pyridine solution to give on the addition of water 2-(2<1>chloropyridine-5<1>-sulphonamide) pyridine which on treatment with ammonia in the presence of cuprous chloride is converted into 2-(2<1>-aminopyridine-5<1>-sulphonamido) pyridine. (5) 2-aminopyridine-5-sulphonyl chloride is treated with benzylamine in alcohol solution to give 2-aminopyridine-5-sulphonbenzylamide. (6) A pyridine solution of p-amino acetonilide is treated with 2-amino-pyridine-5-sulphonyl chloride. On treatment with hydrochloric acid there is obtained 2-amino-pyridine-5-sulphon-4<1>- amino-anilide. (7) 2-amino-pyridine-5-sulphonyl chloride is added to a dilute caustic soda solution of sulphonilamide to give 2-amino-pyridine- 5-sulphonamido-benzene-4<1>-sulphonamide. (8) 2-amino-pyridine-5-sulphonyl chloride is added to an alcoholic solution of methylamine to give 2-amino-pyridine-5-sulphon-methylamide. (9) 2-amino-pyridine-5-sulphonyl chloride is added to aqueous diethylamine to give 2-aminopryidine-5-sulphon-diethylamide. (10) 2-aminopyridine is added to chlorosulphonic acid, the product is poured on to ice and neutralised with caustic soda to give 2-amino-pyridine-5-sulphonyl chloride in the form of an oil which may be used directly to prepare the sulphonamide derivatives of examples 1-6 and 7-9 or it may be purified by crystallization. (11) 2-chloropyridine-5-sulphonyl chloride is added to a pyridine solution of p-amino-acetanilide to give 2-chloropyridine-5-sulphon-4<1>-acetamidoanilide. This on heating with strong ammonia gives 2-amino-pyridine-5 - sulphon 4<1>- aminoanilide. (12) 2-chloropyridine-5-sulphonyl chloride is added to a pyridine solution of sulphonilamide to give 2-chloropyridine-5-sulphonamidobenzene-41-sulpbonamide which on treatment with ammonia is converted into 2-aminopyridine-5- sulphonamidobenzene-4<1>-sulphonamide. Specifications 512,145 and 517,272 are referred to.