DE1020632B - Process for the preparation of 5- (p-bromophenyl) -5-cyclopropylhydantoin - Google Patents
Process for the preparation of 5- (p-bromophenyl) -5-cyclopropylhydantoinInfo
- Publication number
- DE1020632B DE1020632B DEC13603A DEC0013603A DE1020632B DE 1020632 B DE1020632 B DE 1020632B DE C13603 A DEC13603 A DE C13603A DE C0013603 A DEC0013603 A DE C0013603A DE 1020632 B DE1020632 B DE 1020632B
- Authority
- DE
- Germany
- Prior art keywords
- bromophenyl
- cyclopropylhydantoin
- preparation
- cyclopropyl
- hydantoin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 5- (p-bromophenyl) -5-cyclopropylhydantoin Chemical compound 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 3
- 239000001099 ammonium carbonate Substances 0.000 claims description 3
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 3
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 3
- QTHHOINSCNBYQO-UHFFFAOYSA-N (4-bromophenyl)-cyclopropylmethanone Chemical compound C1=CC(Br)=CC=C1C(=O)C1CC1 QTHHOINSCNBYQO-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- YNUMJKGENBAOAZ-UHFFFAOYSA-N 5-cyclopropyl-5-phenylimidazolidine-2,4-dione Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1CC1 YNUMJKGENBAOAZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UDTWZFJEMMUFLC-UHFFFAOYSA-N Nirvanol Chemical compound C=1C=CC=CC=1C1(CC)NC(=O)NC1=O UDTWZFJEMMUFLC-UHFFFAOYSA-N 0.000 description 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- KXPIQHAXIWUWQB-UHFFFAOYSA-N bis[1-(4-bromophenyl)cyclopropyl]methanone Chemical compound C1=CC(Br)=CC=C1C1(C(=O)C2(CC2)C=2C=CC(Br)=CC=2)CC1 KXPIQHAXIWUWQB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von 5-(p-Bromphenyl)-5-cyclopropylhydantoin
Es wurde gefunden, daB das 5-(p-Bromphenyl)-5-cyclopropyl-hydantoin eine stark ausgeprägte
antikonvulsivische Wirkung zeigt, wie aus folgender Tabelle hervorgeht:
Beispiel Eine Lösung von 20,5 g p-Bromphenyl-cyclopropylketon in 100 ccm Alkohol gibt man zu einer Mischung von 27 g Ammoniumcarbonat, 11 g Kaliurncyanid und 100 ccm konzentriertem Ammoniak und erhitzt das Ganze im Schüttelautoklav 18 bis 20 Stunden auf 115 bis 120°.Example A solution of 20.5 g of p-bromophenyl cyclopropyl ketone in 100 cc of alcohol is added to a mixture of 27 g of ammonium carbonate and 11 g of potassium cyanide and 100 ccm concentrated ammonia and heat the whole thing in the shaking autoclave 18 up to 20 hours at 115 to 120 °.
Nach dem Erkalten wird von geringen Verunreinigungen abgetrennt, die klare Lösung mit dem doppelten Volumen Wasser verdünnt und mit verdünnter Salzsäure angesäuert. Nach Lösen in verdünnter Natronlauge, Behandeln mit Aktivkohle, Wiederausfällen mit Salzsäure und Umkristallisieren aus Eisessig schmilzt das 5-(p-Bromphenyl)-5-cyclopropyl-hydantoin bei 228 bis 229°.After cooling, the minor impurities are separated clear solution diluted with twice the volume of water and diluted with dilute hydrochloric acid acidified. After dissolving in dilute sodium hydroxide solution, treatment with activated charcoal, reprecipitation the 5- (p-bromophenyl) -5-cyclopropyl-hydantoin melts with hydrochloric acid and recrystallization from glacial acetic acid at 228 to 229 °.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC13603A DE1020632B (en) | 1956-08-30 | 1956-08-30 | Process for the preparation of 5- (p-bromophenyl) -5-cyclopropylhydantoin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC13603A DE1020632B (en) | 1956-08-30 | 1956-08-30 | Process for the preparation of 5- (p-bromophenyl) -5-cyclopropylhydantoin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1020632B true DE1020632B (en) | 1957-12-12 |
Family
ID=7015480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC13603A Pending DE1020632B (en) | 1956-08-30 | 1956-08-30 | Process for the preparation of 5- (p-bromophenyl) -5-cyclopropylhydantoin |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1020632B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3209009A (en) * | 1965-09-28 | Pons ctal |
-
1956
- 1956-08-30 DE DEC13603A patent/DE1020632B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3209009A (en) * | 1965-09-28 | Pons ctal |
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