CH296484A - Process for the preparation of 5- (o-oxy-phenyl) -1-methyl-hydantoin. - Google Patents
Process for the preparation of 5- (o-oxy-phenyl) -1-methyl-hydantoin.Info
- Publication number
- CH296484A CH296484A CH296484DA CH296484A CH 296484 A CH296484 A CH 296484A CH 296484D A CH296484D A CH 296484DA CH 296484 A CH296484 A CH 296484A
- Authority
- CH
- Switzerland
- Prior art keywords
- hydantoin
- methyl
- phenyl
- oxy
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 8
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 4
- 150000002466 imines Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 125000005219 aminonitrile group Chemical group 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal cyanide Chemical class 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001787 epileptiform Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 5-(o-Oxy-phenyl)-1-methyl-hydantoin. Das Schweizer Patent Nr.292594 bezieht sieh auf ein Verfahren zur Herstellung von 5-(p-Allyloxy-phenyl)-5-methyl-hydantoin, da durch gekennzeichnet, dass man p-Allyloxy- < icetophenon mit Alkalicyanid und Ammo- niumcarbonat umsetzt.
Vorliegendes Patent bezieht. sich nun auf ein Verfahren zur Herstellung von 5-(o-Oxy- l)henyl )-1-niethyl-hydantoin, dadurch gekenn zeichnet, dass man Salicylaldehyd mit Methyl- ainin zum entsprechenden Imin umsetzt, die ses mittels Blausäure in das Aminonitril über- i'ühil., letzteres mit. Alkalicyanat behandelt und verseift.
Das so erhaltene weisse, leicht gelbstichige a-(o-Oxy-phenyl)-1-methyl-hydantoin schmilzt bei 273 bis 2740.
Der Endstoff soll besonders zur Beha.nd- hm- der Erseheinungen, die den epileptifor- inen Krankheitszuständen eigen sind, verwen det werden.
<I>Beispiel</I> 7.u 366g (3 Mol) Salicylaldehyd werden mater Rühren und guter Kühlung langsam 96 llethylamin (3,1 Mol) aus der Bombe eingeleitet. Nach Beendigung des Einleitens wird noch 1/2 Stunde bei 60 im Wasserbad ge- rülirt.. Man erhält so eine Lösung von Salicyl- < ildehyd-Methylimin.
Zu 1,3 Liter 75 % iger Essigsäure werden unter Rühren bei 0 bis 5 im Kältebad in Por- tionen 114 g Kaliiuncyanicl zugegeben. Dann wird bei der gleichen Temperatur die obige Iminlösung zugetropft. Anschliessend werden abermals bei 0 bis 5 111 g Kaliumcyanid in Portionen zugegeben. Die Reaktionsmischung wird unter Rühren auf 0 abgekühlt. Dann werden in Portionen 261 g Kaliumcyanat zu gegeben.
Die Masse wird innerhalb 1 Stunde langsam auf 70 erwärmt und 15 Minuten bei dieser Temperatur gehalten. Nach raschem Abkühlen auf 30 lässt man innerhalb 15 Mi nuten 900 cm3 konz. Salzsäure einlaufen und rührt dann 1 Stunde bei 80 bis 90 im Wasser bad. Die etwas abgekühlte Lösung wird dann in etwa 8 Liter eiskaltes Wasser gegossen und 2 Tage in Eis stehengelassen. Das Ausgefal lene wird abgesaugt und mit Wasser ge waschen. Das Filtrat wird mit der gleichen Menge Wasser verdünnt. Nach 2tägigem Ste- benlassen in Eis wird abermals das Ausgefal lene abgesaugt und mit dem 1. Teil vereinigt.
Die erhaltenen gelblichen Kristallabscheidun- gen werden aus viel Alkohol und Kohle, dann aus Dioxan umkristallisiert und im Vakuum getrocknet.
Das erhaltene weisse, leicht gelbstichige 5 (o-Oxy-phenyl)-1-methyl-hydantoin schmilzt bei 273 bis 27411.
Process for the preparation of 5- (o-oxy-phenyl) -1-methyl-hydantoin. Swiss Patent No. 292594 relates to a process for the production of 5- (p-allyloxyphenyl) -5-methyl-hydantoin, characterized in that p-allyloxy- icetophenone is reacted with alkali metal cyanide and ammonium carbonate.
This patent relates. now on a process for the production of 5- (o-oxy- l) henyl) -1-niethyl-hydantoin, characterized in that salicylaldehyde is reacted with methyl ainine to form the corresponding imine, which is converted into the aminonitrile using hydrocyanic acid - i'ühil., the latter with. Treated and saponified alkali cyanate.
The white, slightly yellowish a- (o-oxy-phenyl) -1-methyl-hydantoin thus obtained melts at 273 to 2740.
The end product should be used especially for treating the appearances peculiar to the epileptiform states of illness.
<I> Example </I> 7. 366 g (3 mol) of salicylaldehyde are slowly introduced from the bomb by stirring and thorough cooling. When the introduction is complete, the mixture is stirred in a water bath at 60 for a further 1/2 hour. A solution of salicylaldehyde methylimine is obtained in this way.
114 g of potassium cyanide are added in portions to 1.3 liters of 75% acetic acid with stirring at 0 to 5 in the cold bath. The above imine solution is then added dropwise at the same temperature. Then again at 0 to 5 111 g of potassium cyanide are added in portions. The reaction mixture is cooled to 0 while stirring. Then 261 g of potassium cyanate are added in portions.
The mass is slowly heated to 70 within 1 hour and held at this temperature for 15 minutes. After rapid cooling to 30 minutes, 900 cm3 of conc. Run in hydrochloric acid and then stir for 1 hour at 80 to 90 in a water bath. The slightly cooled solution is then poured into about 8 liters of ice-cold water and left to stand in ice for 2 days. The precipitated is suctioned off and washed ge with water. The filtrate is diluted with the same amount of water. After standing in ice for 2 days, the precipitated material is again suctioned off and combined with the first part.
The yellowish crystal deposits obtained are recrystallized from a large amount of alcohol and charcoal, then from dioxane and dried in vacuo.
The white, slightly yellowish 5 (o-oxy-phenyl) -1-methyl-hydantoin obtained melts at 273 to 27411.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE296484X | 1950-03-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH296484A true CH296484A (en) | 1954-02-15 |
Family
ID=6090394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH296484D CH296484A (en) | 1950-03-06 | 1951-03-02 | Process for the preparation of 5- (o-oxy-phenyl) -1-methyl-hydantoin. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH296484A (en) |
-
1951
- 1951-03-02 CH CH296484D patent/CH296484A/en unknown
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