http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-193618-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_9a4356d10af90df67be11d97fbd96394 http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_904aa0b09af7d43f8b91c624c23babdc http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_deb2df9d17df8999bb1f322a5a888970 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C303-28 |
| classificationIPCAdditional | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C309-73 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C303-28 |
| filingDate | 1922-01-19-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1923-03-01-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-193618-A |
| titleOfInvention | The manufacture of a new chloro-ethyl-ester and the treatment of phenols, alcohols and amino compounds therewith |
| abstract | p-Toluenesulphonic-b -chlorethyl ester is obtained by heating p-toluenesulphonic chloride with glycol chlorhydrin; it may be distilled in vacuo. In an example an excess of the glycol chlorhydrin is used. Ethylene-ethers and chlorethylethers are obtained by interaction of the above-mentioned p-toluene sulphonic chlorethyl ester and alcohols, phenol, cresols, p-nitro-o-cresol, naphthols, or aminophenols; in the latter case the amino groups are first protected; o- or p-nitro-phenols do not readily give ethers by this process. The chlorethylethers obtained from the phenols &c. react with arylamines or monoalkylamines such as ethylaniline to give b -phenoxyethyl derivatives of the said bases; these derivatives yield nitroso compounds. According to examples, the following compounds are prepared:- (1) phenyl-b -chlorethyl ether and some diphenylethylene ether from phenol and p-toluenesulphonic-b -chlorethyl ester, and a - or b -naphthyl-b -chlorethyl ether and a - or b -naphthylethylene ether from a - or b -naphthol; the b -naphthyl-b -chlorethyl ether, heated with dimethylamine under pressure, gives b -naphthyl-b -dimethylaminoethyl ether, of which the hydrochloride has a local anaesthetic action; the b -naphthyl-b -chlorethyl ether may also be nitrated, reduced and the amino compound boiled with amyl alcohol, potassium carbonate and copper powder, to give an a : b -naphthylene morpholine: (2) benzyl-b -chlorethyl ether from benzyl alcohol; with diethylamine it yields b -diethylaminoethylbenzyl ether which forms an ammonium iodide with ethyl iodide: (3) o- and p-acetamino-b -chlorethyl ethers from o-acetaminophenol and acetyl - p - acetaminophenol, CH3.CO.NH.C6H4.O.CO.CH3, respectively. Ethylenediamine derivatives, chlorethylamines, and piperazine derivatives are prepared by interaction of p-toluenesulphonic-b -chlorethyl ester and amines. In examples the preparation of the following compounds is described:-(1) diphenylethylene diamine and diphenylpiperazine from aniline: (2) sym-dimethyldiphenylethylene diamine and b -chlorethylmethylaniline from methylaniline; the reaction mass is steam distilled when the diamine remains behind; the distillate, which contains the b -chlorethylmethylaniline is freed from methylaniline by treatment with p-toluenesulphonic chloride. b -Chlorethylmethylaniline condenses with b -naphthol in presence of alkali to form b -naphthyloxyethylmethylaniline. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-2567778-A |
| priorityDate | 1922-01-19-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 73.