http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-575005-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_73ee0bacab5a7576a6a3244747f6ea99 http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_3f72954e781eb153a02bcd6dcecfbe75 http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_4b2d259c31f60b58a0d054d69d8ac69a |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D239-52 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D239-69 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D239-52 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D239-69 |
| filingDate | 1943-12-01-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1946-01-30-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-575005-A |
| titleOfInvention | New sulphanilamide derivatives |
| abstract | 2 - p - (Amino or acylamino) - benzenesulphonamido-4 : 6-dialkoxypyrimidines, useful as anti-bacterial agents, wherein the 5-position may optionally bear a methyl or ethyl group and wherein the two alkoxy groups, which may be alike or different, jointly contain not more than 6 carbon atoms, are produced by reaction of the appropriate 2-amino-4 : 6-dialkoxypyrimidine (a) with a p-acylaminobenzenesulphonyl halide and, if desired, hydrolysis of the acyl amino group in the product or (b) with a p-nitrobenzenesulphonyl halide, and reduction of the nitro group in the product. The reaction is conveniently effected in an anhydrous solvent, preferably in the presence of an acid-binding agent; alternatively a basic solvent such as pyridine or triethylamine may be used. The products carrying a free amino group may be solubilised by interaction with aldehydes and bisulphites or hydrosulphites. Reduction of the nitro group may be effected (a) by heating in alcoholic or aqueous medium with iron filings and dilute hydrochloric acid, (b) by heating in aqueous solution with sodium mono- or di-sulphide, (c) by hydrogenation in an inert organic liquid, using Raney nickel or palladium as catalyst. Examples relate to the condensation of (1) p-nitrobenzenesulphonyl chloride with 2-amino-4 : 6-dimethoxypyrimidine in pyridine, followed by reduction by heating with iron filings in b -ethoxyethanol containing aqueous hydrochloric acid; (2) p-nitrobenzenesulphonyl chloride with 2-amino-4 : 6-diethoxypyrimidine followed by similar reduction of the nitro group; (3) p - nitrobenzenesulphonyl chloride with 2-amino-4 : 6-di-n-propoxypyrimidine, followed by similar reduction of the nitro group; (4) p - nitrobenzenesulphonylchloride with 2-amino-4 : 6-di-isopropoxypyrimidine, followed by similar reduction of the nitro group; (5) p - acetylaminobenzene sulphonyl chloride with 2-amino-4-methoxy-6-ethoxypyrimidine, followed by hydrolysis of the acetylamino group with aqueous sodium hydroxide and isolation of the free base by acidification with acetic acid; (6) p-acetylaminobenzenesulphonyl chloride with 2-amino-5-methyl-4 : 6-dimethoxypyrimidine, followed by further treatment as in (5); (7) p-acetylaminobenzenesulphonyl chloride with 2-amino-5-ethyl-4 : 6-dimethoxypyrimidine, followed by further treatment as in (5); (8) p-acetylamino-benzenesulphonyl chloride with 2-amino-4 : 6-dimethoxypyrimidine in pyridine. Specifications 547,976, 555,865 and 571,014 are referred to. 2-Amino-4 : 6-dialkoxypyrimidines are obtained by interaction of a sodium alkoxides and the appropriate 2-amino-4 : 6-dichloropyrimidine. 2 - Amino - 4 - methoxy - 6 - ethoxypyrimidine is obtained by interaction of 2-amino-4-chloro-6-methoxy-pyrimidine with sodium ethoxide in boiling xylene. 2 - Amino - 5 - methyl or ethyl - 4 : 6 - dimethoxypyrimidine is obtained by interaction of 2-amino-5-methyl or ethyl-4 : 6-dihydroxypyrimidine with phosphorus oxychloride and subsequent treatment of the dichloro compound so formed with sodium methoxide in boiling xylene. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4759460-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-3091610-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-2703800-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-3214335-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-3203951-A |
| priorityDate | 1943-12-01-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 67.