http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-607367-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_fd9f36df06271a59df790e5021907cdc |
| filingDate | 1946-01-31-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1948-08-30-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-607367-A |
| titleOfInvention | A process for the manufacture of a thiophane derivative |
| abstract | A thiophane derivative having the activity of biotin is manufactured from a lower alkyl ester of 2-(o -methoxybutyl)-thiophane-3 : 4f dicarboxylic acid (obtained by the process o-Specification 589,210) by treating it with hydrazine hydrate and, after separation of a crystalline dihydrazide, evaporating the mother liquor and treating the residue in hydrochloric acid solution with sodium nitrite, decomposing the resulting acid azide by heating with alcohol to yield the 3 : 4-diurethane, evaporating the solution under reduced pressure and separating from the benzene solution of the residue a fraction capable of being eluted comparatively easily by chromatography, converting the more difficulty elutable fraction into the dihydrobromide of 2-(o -bromobutyl)-3 : 4-diaminothiophane by heating with hydrobromic acid, treating the resulting salt with phosgene in the presence of alkali and the product successively with potassium cyanide and a saponifying agent, and, after acidification, isolating the 2 - (o - carboxybutyl) - 3 : 4 - (imidazolidone - 21) - thiophane in crystalline form, e.g. by esterification, crystallization of the ester from the eluate after chromatographic purification, and saponification. In an example, the procedure described for the preparation of Sample II of Specification 589,210 is followed up to the point of adsorbing the benzene solution of the diurethane on to an aluminium oxide column, and, after elution with benzene, a second fraction is eluted with chloroform, the eluate evaporated to dryness under reduced pressure, the product heated with hydrobromic acid solution, excess of which is evaporated in vacuo, the residue is dissolved in aqueous caustic soda and treated with a solution of phosgene in toluene, the product is isolated and refluxed with potassium cyanide in ethyl alcohol, the product is saponified with aqueous potassium hydroxide, the acid is liberated with hydrochloric acid, dissolved in methyl alcohol and esterified with diazomethane, a solution of the ester in chloroform is adsorbed on to an aluminium oxide column, which is washed with chloroform and then eluted with acetone, the purified ester is crystallized from the eluate, recrystallized from ethyl acetate or a methyl alcohol-ether mixture and saponified with aqueous caustic soda, and the sterically uniform dl-2-(o -carboxybutyl)-3 : 4-(imidazolidone-21)-thiophane is liberated with hydrochloric acid. |
| priorityDate | 1945-02-02-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
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