Patent GB-555865-A (GB)
Title: Sulphonamido pyrimidines
IPC: C07D239/69
Filed: 1941-03-08
Abstract: 555,865. Sulphonamido pyrimidines. AMERICAN CYANAMID CO. March 8, 1941, Nos. 3174 and 3175. Convention dates, March 1, 1940 and Oct. 15, 1940. Samples furnished. [Class 2 (iii)] p-Substituted benzene-sulphonamido-pyrimidenes are made by reacting a benzene-sulphonyl halide, e.g. a chloride substituted in the para position by an amino group or a group convertible thereto by hydrolysis, reduction or by reaction with ammonia or an amine such as an acylamino, nitro, halogen or azo group, with an amino-pyrimidine. The products are of the general formula where R is a halogen, nitro, azo, amino or substituted amino group, e.g. alkylamino, arylamino, aralkylamino, acylamino or monoaldose amino, X is H, an alkyl group or a metal, Py is a pyrimidine substituted or unsubstituted and n is a small integer. The mono-aldose amino compounds are'made from the corresponding amino compounds by reaction with a mono aldose sugar such as galactose or glucose preferably in a solvent such as ethanol. Free hydrogen halide obtained during the reaction with a sulphonyl halide is removed by effecting the reaction in a basic medium, e.g. aqueous sodium hydroxide, triethylamine and pyridine and solvents, e.g. dioxane, acetone and benzene are specified. Alkali metal or heavy metal, e.g. gold, lead, copper and iron, salts of the products are also described. Examples describe the preparation of the following compounds by the above methods (1) 5-(N<SP>4</SP>- acetylsulphanilamido) - 2, 4 - dihydroxy-, (2) 5 - (sulphanilamido) - 2, 4 - dihydroxy-, (3) 5 - (p - nitrobenzene sulphonamido) - 2, 4 - dihydroxy-, (4) 5 - (N<SP>4</SP> -acetylsulphanil - - amido)-, (5) 5 - (sulphanilamido)-, (6) 4 - (p - nitrobenzenesulphonamido)-, (7) and (9) 4 - (sulphanilamido)-, (8) 4 - (N<SP>4</SP> - acetyl - sulphanilamido)-, (10) 2 - (p - nitrobenzene - sulphonamido)-, (11) and (13) 2 - (sulphanil - amido)-, (12) 2 - (N<SP>4</SP> - acetylsulphanilamido) -, (14) 4 - p - nitrobenzenesulphonamido 2 - methoxy-, (15) 4 - sulphanilamido - 2 - methoxy-, (16) 2 - (p - nitrobenzene - sulphon - amido) 4 - methoxy-, (17) 2 - sulphanilamido- 4 - methoxy-, (18) 2 - (p - nitrobenzene - sulphonamido) - 4, 6 - dimethyl-, (19) 2 - sulphanlamido - 4, 6 - dimethyl-, (20) 2 - N<SP>1</SP> - methyl - sulphanilamido-, (21) 4 - p - chloro - benzene - sulphamido-, (this pyrimidine may be reacted with ammonia or amines, e.g. methylamine, aniline or benzyl amine to yield the corresponding substituted 4-N<SP>4</SP> pyrimidine), (22) azobenzene - p -, p<SP>1</SP> - (di - 2 - sulphon - amido)-, (23) 5 - (N<SP>4</SP> - acetylsulphanilamido) - 2 - acetylamino-, (24) 5 - sulphanilamido - 2 - amino, (25) 5 - (p - nitrobenzenesulphonamido) - 2 - methoxy-, (26) 5 - sulphanilamido - 2. - methoxy-, (27) 2 - (N<SP>4</SP> - acetylsulphanilamido) - 4 - ethoxy,- (28) 2 - sulphanilamido - 4 - ethoxy, (29) 2, 5 - di (p - nitrobenzene - sulphonamido)-, (30) 2, 5 - disulphanilamido-, (31) 2 - (p - nitrobenzene - sulphonamido) - 5 - chloro-, (32) 2 - sulphanilamido - 5 - chloro-, (33) sodium salt of 2 - sulphanilamido-, (34) copper salt of 2 - sulphanilamido-, (35) the glucose derivative of 2-sulphanilamido- and (36) 2-(N<SP>4</SP>-benzylsulphanilamido)-pyrimidine. Examples (35) and (36) relate to two typical samples which have been furnished. The Specification as open to inspection under Sect. 91 states that in some cases the products may also be made by reacting a halogen substituted pyrimidine with an N<SP>4</SP>-acylsulphanilamide in the presence of an alkali with subsequent hydrolysis of the acyl group. In examples (23) N<SP>4</SP>-acetylsulphanilamide is treated with 2-chloro-4, 6-dimethylpyrimidine in the presence of potassium carbonate and copper powder to yield 2-N<SP>4</SP>-acetylsulphanilamido-4, 6-dimethyl pyrimidine which is hydrolysed to the free amine, (24) 2-sulphanilamidopyrimidine is diazotized and coupled with 7-acetylamino-1-hydroxynaphthalene-3, 6-disulphonic acid to yield 4<SP>1</SP>-(N-(2-pyrimidyl) sulphonamido) - 2 - azo - 7 - acetylamino - 1 - hydroxynaphthalene - 3, 6 - disulphonic acid and in (29) 2-(N<SP>4</SP>-acetylsulphanilamido)-4- methyl - pyrimidine and (30) 2 - sulphanil - amido - 4 - methylpyrimidine are made by methods described above. This subjectmatter does not appear in the Specification as accepted.