CH171978A - Process for the preparation of a barbituric acid derivative. - Google Patents
Process for the preparation of a barbituric acid derivative.Info
- Publication number
- CH171978A CH171978A CH171978DA CH171978A CH 171978 A CH171978 A CH 171978A CH 171978D A CH171978D A CH 171978DA CH 171978 A CH171978 A CH 171978A
- Authority
- CH
- Switzerland
- Prior art keywords
- ethyl
- preparation
- acid
- methyl
- barbituric acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- DNZPLHRZXUJATK-UHFFFAOYSA-N 2-sulfanylidene-5-[[5-[2-(trifluoromethyl)phenyl]furan-2-yl]methyl]-1,3-diazinane-4,6-dione Chemical compound FC(F)(F)C1=CC=CC=C1C(O1)=CC=C1CC1C(=O)NC(=S)NC1=O DNZPLHRZXUJATK-UHFFFAOYSA-N 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000012022 methylating agents Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- -1 aromatic sulfonic acid methyl ester Chemical class 0.000 description 2
- ALARQZQTBTVLJV-UHFFFAOYSA-N mephobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)N(C)C1=O ALARQZQTBTVLJV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NZMIRLKHMFERSX-UHFFFAOYSA-N 2-phenylethyl 2-cyanoacetate Chemical compound N#CCC(=O)OCCC1=CC=CC=C1 NZMIRLKHMFERSX-UHFFFAOYSA-N 0.000 description 1
- HTEHILLCBQWTLP-UHFFFAOYSA-N 5-phenyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1NC(=O)NC(=O)C1C1=CC=CC=C1 HTEHILLCBQWTLP-UHFFFAOYSA-N 0.000 description 1
- 241001397173 Kali <angiosperm> Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Yerfahren zur Darstellung eines Barbitursäurederivates. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von 1-Methyl- 5-äthyl- 5-phenylbarbitursäure. Das Verfahren ist dadurch gekennzeichnet, dass man auf 2,4- Diimino-3-cyan-5-äthyl#5-phenyl-barbitursäure ein Methylierungsmittel einwirken lässt und das Methylierungsprodukt mit einem Versei fungsmittel behandelt. Als Methylierungs- mittel verwendet man z.
B. Methyljodid, Dimethylsulfat oder einen aromatischen Sul- fonsäuremethylester in Gegenwart von Al kali, zweckmässig Alkalialkoholat. Die Re aktion wird normalerweise in Gegenwart eines Löse- oder Verdünnemittels ausgeführt. Zweckmässig kommen dafür Alkohole zur Verwendung. Als Verseifungsmittel kommen vorzugsweise verdünnte Mineralsäuren in Frage.
Das in der beschriebenen Weise erhält liche neue Produkt bildet farblose Kristalle vom Schmelzpunkt 176 0. Es ist in Wasser praktisch unlöslich, löst sich aber 111 was- serigen Alkalien. Es soll therapeutische An wendung finden.
<I>Beispiel:</I> 46 Teile Natriummetall löst man in 300 Teilen Methanol, gibt hierzu 92 Teile Di- cyandiamid und 217 Teile Phenyläthylcyan- essigsäureäthylester (Kpis 155 ) und erhitzt etwa 10 Stunden am Rückflusskühler auf 70-800. Hierauf fügt man zu der abgekühl ten, die 2,4-Diimino-3-cyan-5-äthyl-5-phenyl- barbitursäure enthaltenden Lösung 240 Teile Dimethylsulfat und sorgt dafür, dass die Temperatur nicht über 500 steigt.
Nach mehrstündigem Stehen destilliert man das Methanol auf dem Wasserbad ab und ver kocht den Rückstand mit dem sechsfachen seines Gewichtes 25 %iger Schwefelsäure während etwa 5 Stunden. Nach dem Erkalten saugt man die abgeschiedene 1-Methyl-5- phenyl-5-äthylbarbitursä,ure ab und löst sie aus der dreizehnfachen Menge Alkohol um. Man erhält feine farblose Kristalle vom F. 176 .
Für die Alkylierung können an Stelle von Dimethylsulfat und Toluolsulfosäure- alkylestern sinngemäss auch Alkylhalogenide, wie z. B. Jodäthyl, gegebenenfalls unter Zu satz von Katalysatoren, Verwendung finden.
Method for the preparation of a barbituric acid derivative. The subject of the present patent is a process for the preparation of 1-methyl-5-ethyl-5-phenylbarbituric acid. The process is characterized in that a methylating agent is allowed to act on 2,4-diimino-3-cyano-5-ethyl # 5-phenylbarbituric acid and the methylation product is treated with a saponifying agent. The methylating agent used is z.
B. methyl iodide, dimethyl sulfate or an aromatic sulfonic acid methyl ester in the presence of Al kali, expediently alkali metal alcoholate. The reaction is usually carried out in the presence of a solvent or diluent. Alcohols are expediently used for this. Dilute mineral acids are preferably used as saponification agents.
The new product obtained in the manner described forms colorless crystals with a melting point of 176 0. It is practically insoluble in water, but dissolves in aqueous alkalis. It should find therapeutic use.
Example: 46 parts of sodium metal are dissolved in 300 parts of methanol, 92 parts of dicyandiamide and 217 parts of phenylethylcyanoacetate (boiling point 155) are added and the mixture is heated to 70-800 for about 10 hours on a reflux condenser. 240 parts of dimethyl sulfate are then added to the solution containing 2,4-diimino-3-cyano-5-ethyl-5-phenylbarbituric acid, and it is ensured that the temperature does not exceed 500.
After standing for several hours, the methanol is distilled off on a water bath and the residue is boiled with six times its weight of 25% strength sulfuric acid for about 5 hours. After cooling, the separated 1-methyl-5-phenyl-5-ethylbarbituric acid is suctioned off and it is dissolved from thirteen times the amount of alcohol. Fine, colorless crystals of F. 176 are obtained.
For the alkylation, instead of dimethyl sulfate and toluenesulfonic acid alkyl esters, alkyl halides, such as. B. iodoethyl, optionally with the addition of catalysts, use.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE171978X | 1931-12-31 | ||
| CH169179T | 1932-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH171978A true CH171978A (en) | 1934-09-15 |
Family
ID=25718684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH171978D CH171978A (en) | 1931-12-31 | 1932-09-05 | Process for the preparation of a barbituric acid derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH171978A (en) |
-
1932
- 1932-09-05 CH CH171978D patent/CH171978A/en unknown
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