http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-704978-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_9e28032b4dae483384b2f28cb3ee45bc |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D233-72 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D233-72 |
| filingDate | 1951-03-06-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1954-03-03-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-704978-A |
| titleOfInvention | Manufacture of new hydantoin compounds |
| abstract | The invention comprises compounds of the formula <FORM:0704978/IV(b)/1> wherein one X means hydrogen, the other X means hydroxy, alkoxy containing halogen or dialkylamino or a double bond, and one Y means hydrogen, another Y means alkyl (including aralkyl and haloalkyl) and the remaining Y means hydrogen or alkyl (including aralkyl and haloalkyl). The compounds have an antiepileptic and a hypnotic action. They may be prepared by reacting with a compound of the formula <FORM:0704978/IV(b)/2> wherein Y means hydrogen or alkyl (including aralkyl and haloalkyl) an amine or ammonia and an alkali metal cyanide in the presence of an acid or with ammonium carbonate and alkali cyanide with or without overpressure of carbon dioxide. Alternatively the above compound may be reacted with a primary amine, the imine thus obtained converted with hydrocyanic acid (or alkali cyanide and an acid) into an aminonitrile, and the latter compound treated with an alkali cyanate and saponified with acids. The products may also be produced by acting with alcohol, caustic soda solution and urea on substituted benzoles. Into the hydantoins produced may be introduced alkyl radicals (when X and Y are hydrogen), bromine atoms (when X and Y are unsaturated) or alkylamino groups. In examples (1) 5-(o-hydroxyphenyl)-5-methylhydantoin is produced by reacting o-hydroxy acetophenone, potassium cyanide and ammonium bicarbonate in aqueous ethanol under carbon dioxide pressure. Similarly prepared are (2) 5-(p-allyloxyphenyl)-5-methylhydantoin from p-allyloxy-acetophenone (obtained from p-hydroxy-acetophenone and allyl bromide) potassium cyanide and ammonium carbonate; (3) 5-o-(b -diethylaminoethoxy - phenyl - 5 - propyl - hydantoin by reacting o (b -diethylamino-ethoxy)-butyro - phenone (prepared from o-hydroxybutyrophenone) and diethylamino chlorethane), potassium cyanide and ammonium carbonate; (6) 5 - p - phenoxyphenyl - 5 - methyl - hydantoin from p-phenoxy acetophenone, potassium cyanide and ammonium carbonate. In further examples are prepared (4) 5-(o-hydroxyphenyl)-1-N (n) butyl-hydantoin by reaction of salicylaldehyde with butyraldehyde to form the imine, reaction of the product firstly with potassium cyanide and acetic acid and then with potassium cyanate, followed by hydrolysis with hydrochloric acid; (5) 5-p (b -d -dibromopropoxyphenyl) - 5 - methyl hydantoin by bromination of the product of example (2); (7) 3 - methyl - 5 - methyl - 5 - p - allyloxy - phenyl - hydantoin by treatment of 5-p-allyloxphenyl - 5 - methyl - hydantoin with dimethyl sulphate. A table lists 26 compounds with variation of X and Y, the group <FORM:0704978/IV(b)/3> being selected from o- and p-hydroxy-, o and p-allyloxy-, o- and p-b , g -dibromopropoxy-, and o- and p- (b -diethylamino-ethoxy)-phenyl, and the groups at Y being selected from hydrogen, methyl, ethyl, n-propyl, allyl, benzyl, d b -phenylethyl, and b , g -dibromo-propyl. |
| priorityDate | 1950-03-06-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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