CH90592A - Process for the preparation of isopropylallylbarbituric acid. - Google Patents
Process for the preparation of isopropylallylbarbituric acid.Info
- Publication number
- CH90592A CH90592A CH90592DA CH90592A CH 90592 A CH90592 A CH 90592A CH 90592D A CH90592D A CH 90592DA CH 90592 A CH90592 A CH 90592A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- acid
- preparation
- isopropylallylbarbituric
- solution
- Prior art date
Links
- UORJNBVJVRLXMQ-UHFFFAOYSA-N aprobarbital Chemical compound C=CCC1(C(C)C)C(=O)NC(=O)NC1=O UORJNBVJVRLXMQ-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229960003153 aprobarbital Drugs 0.000 title description 3
- 239000002253 acid Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- -1 allyl halides Chemical class 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 230000020477 pH reduction Effects 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- GFPIGNBQTXNNAG-UHFFFAOYSA-N 5-propan-2-yl-1,3-diazinane-2,4,6-trione Chemical compound CC(C)C1C(=O)NC(=O)NC1=O GFPIGNBQTXNNAG-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/62—Barbituric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Isopropylallylbarbitursättre. Gegenstand der vorliegenden =Erfindung ist ein Verfahren zur Darstellung von Iso- propylallylbai@bitursliure; welches darin besteht, dass man auf die Alkaliverbindungen der Mono- isopropylbarbitursäure Allylhalogenid bei nie derer Temperatur. und ohne Anwendung von Druck einwirken lässt.
Die Isopropylallylbai,bitursäure bildet farb lose. Kristalle vom Schmelzpunkt 137-138 . Sie ist in Wasser ziemlich schwer; in Al kohol leicht löslich und im Vergleich zu den bekannten Dialkylbarbitursäuren sehr leicht löslich in Aether. Die wässerige Lösung reagiert auf Lackmus neutral. Die neue Ver bindung löst sich in kalter verdünnter Natron lauge und wird aus ihrer alkalischen Lösung durch Ansäuern unverändert abgeschieden.
Die Isopropylallylba rbitursäure soll zu therapeutischen Zwecken Verwendung finden. BeispAel: 170 Gewichtsteile Isopropylbarbitursäure werden mit 500 Gewichtsteilen Wasser über gossen und durch Zufügen von 135 Gewichts teilen 30prozentiger Natronlauge in Lösung gebracht. Nach erfolgter Lösung setzt man 130 U ewichtsteile Allylbromid hinzu und ver rührt emulgierend bei einer inneren Tempe ratur von etwa 250.- Die Reaktion ist an fänglich von einer geringen Wärmeentwicklung , begleitet.
Nach 12 Stunden ist die Reaktion beendet. Die von abgeschiedener Isopropy 1- allylbarbitursäure dünnbreiige Masse wird nach gutem Abkühlen abgesaugt. Die Aus beute beträgt über 80o/0 der theoretisch be- rechneten 11Ienge. Durch einmaliges -Umkri- stallisieren aus verdünntem Alkohol wird die Isopropylallylbarbitursäure rein in Form farb loser Kristalle vom Schmelzpunkt 137-138 erhalten. .
Process for the preparation of isopropylallyl barbiturates. The present invention relates to a process for the preparation of isopropylallylbai @ bitursliure; which consists in the fact that one on the alkali compounds of the mono-isopropylbarbituric acid allyl halide at low temperature. and let it take effect without applying pressure.
The Isopropylallylbai, bituric acid forms colorless. Crystals with a melting point of 137-138. It's quite heavy in water; Easily soluble in alcohol and, compared to the known dialkylbarbituric acids, very easily soluble in ether. The aqueous solution reacts neutrally to litmus. The new connection dissolves in cold, dilute caustic soda and is separated from its alkaline solution unchanged by acidification.
The isopropylallylba rbituric acid is said to be used for therapeutic purposes. Example: 170 parts by weight of isopropylbarbituric acid are poured over 500 parts by weight of water and dissolved by adding 135 parts by weight of 30 percent sodium hydroxide solution. After the solution is complete, 130 parts by weight of allyl bromide are added and the mixture is stirred in an emulsifying manner at an internal temperature of about 250. The reaction is initially accompanied by a slight evolution of heat.
The reaction has ended after 12 hours. The thin-pulpy mass of isopropyl 1-allylbarbituric acid that has separated out is filtered off with suction after cooling well. The yield is over 80o / 0 of the theoretically calculated 11length. A single recrystallization from dilute alcohol gives isopropylallylbarbituric acid in pure form in the form of colorless crystals with a melting point of 137-138. .
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH90592T | 1920-09-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH90592A true CH90592A (en) | 1921-11-01 |
Family
ID=4347867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH90592D CH90592A (en) | 1920-09-17 | 1920-09-17 | Process for the preparation of isopropylallylbarbituric acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH90592A (en) |
-
1920
- 1920-09-17 CH CH90592D patent/CH90592A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH90592A (en) | Process for the preparation of isopropylallylbarbituric acid. | |
| DE539806C (en) | Process for the preparation of isopropylallylbarbituric acid | |
| CH205160A (en) | Method for producing a capillary-active connection. | |
| AT92386B (en) | Process for the preparation of isopropylalkylbarbituric acids. | |
| AT72452B (en) | Process for the preparation of salts of menthol and borneol sulfuric acids. | |
| AT92407B (en) | Process for the preparation of 1-allyl-3,7-dimethylxanthine. | |
| CH242493A (en) | Process for the preparation of a new benzenesulfonamide derivative. | |
| AT207383B (en) | Process for the preparation of sulfonylureas | |
| DE876999C (en) | Process for the production of pellets of 4-aminobenzenesulfonamide | |
| CH239155A (en) | Process for the production of a new benzene sulfonamide derivative. | |
| CH239153A (en) | Process for the production of a new benzene sulfonamide derivative. | |
| CH239158A (en) | Process for the production of a new benzene sulfonamide derivative. | |
| CH239147A (en) | Process for the production of a new benzene sulfonamide derivative. | |
| CH181160A (en) | Process for the preparation of a new heterocyclic sulfonic acid. | |
| CH374981A (en) | Process for the preparation of sulfonylureas | |
| CH239151A (en) | Process for the production of a new benzene sulfonamide derivative. | |
| CH207674A (en) | Process for preparing an aminobenzenesulfonic acid amide compound. | |
| CH276621A (en) | Process for the preparation of p-amino-salicylic acid-n-butylmide. | |
| DE1081001B (en) | Process for the preparation of sulfonylureas | |
| CH226010A (en) | Process for the preparation of 4- (benzylideneaminomethyl) -benzenesulfonamide. | |
| CH239152A (en) | Process for the production of a new benzene sulfonamide derivative. | |
| CH374643A (en) | Process for the preparation of sulfonylureas | |
| CH199674A (en) | Process for the preparation of thymolazophenylsulfonamide. | |
| CH126127A (en) | Process for the preparation of a thiobenzimidazole series gold compound. | |
| CH170087A (en) | Process for the preparation of an oxycarboxylic acid. |