CH171981A - Process for the preparation of a barbituric acid derivative. - Google Patents
Process for the preparation of a barbituric acid derivative.Info
- Publication number
- CH171981A CH171981A CH171981DA CH171981A CH 171981 A CH171981 A CH 171981A CH 171981D A CH171981D A CH 171981DA CH 171981 A CH171981 A CH 171981A
- Authority
- CH
- Switzerland
- Prior art keywords
- sub
- preparation
- dimethyl
- acid derivative
- 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
- VTIMKWYUDLSVRN-UHFFFAOYSA-N 1,5-dimethyl-5-phenyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CC=CC=C1 VTIMKWYUDLSVRN-UHFFFAOYSA-N 0.000 claims description 4
- 239000012022 methylating agents Substances 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 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
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Barbitursäurederivates. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von 1,5-Dime- thyl-5-phenylbarbitursäure. Das Verfahren ist dadurch gekennzeichnet, dass man auf 2-Imino- 3-cyarr-5-methyl-5-pheriylbarbitursäure ein Methylierungsmittel einwirken lässt und das Methylierungsprodukt der Verseifung unter wirft. Als Methylierungsmittel verwendet man z.
B. Methyljodid, Dimethylsulfat oder einen aromatischen Sulfonsäuremethylester in Ge genwart von Alkali, zweckmässig Alkalialko- holat. Die Reaktion wird normalerweise in Gegenwart eines Löse- oder Verdünnungs mittels ausgeführt. Zweckmässig kommen dafür Alkohole zur Verwendung. Als Versei fungsmittel kommen vorzugsweise verdünnte Mineralsäuren in Frage.
Das in der beschriebenen Weise erhält liche neue Produkt bildet Kristalle vom Schmelzpunkt 1540. Es ist in Wasser prak tisch unlöslich, löst sich aber in wässerigen Alkalien. Es soll therapeutische Anwendung finden. <I>Beispiel:</I> In eine methylalkoholische Lösung von 2-imino-3-cyan-5-methyl-5-phenylbarbitursau- rem Natrium, erhalten durch Kondensation von etwa 1 Mol Phenyläthylmalonsäureester mit etwa 1 Mol Dicyandiamid in Gegenwart von etwa 2 Mol Natriummethylat,
lässt man unter Rühren 140 Teile Dimethylsulfat ein laufen, wobei die Temperatur während des Zulaufes unter 50<B>'</B>gehalten wird. Wenn die Reaktionstemperatur zurückgegangen ist, de stilliert man den Methylalkohol ab, versetzt den Rückstand mit der 6fachen Menge seines Gewichtes 20 %iger wässeriger Schwefelsäure und kocht 6 Stunden unter Rühren am Rück flusskühler. Nach dem Erkalten saugt man die kristallinisch abgeschiedene 1,5-Dimethyl- 5-phenylbarbitursäure ab und kristallisiert aus Alkohol um. Man erhält farblose Kristalle vom F. 154 0.
Process for the preparation of a barbituric acid derivative. The subject of the present patent is a process for the preparation of 1,5-dimethyl-5-phenylbarbituric acid. The process is characterized in that a methylating agent is allowed to act on 2-imino-3-cyarr-5-methyl-5-pheriylbarbituric acid and the methylation product is subjected to saponification. The methylating agent used is, for.
B. methyl iodide, dimethyl sulfate or an aromatic sulfonic acid methyl ester in the presence of alkali, conveniently alkali alcohol. 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 saponifying agents.
The new product obtained in the manner described forms crystals with a melting point of 1540. It is practically insoluble in water, but dissolves in aqueous alkalis. It should find therapeutic application. <I> Example: </I> In a methyl alcoholic solution of 2-imino-3-cyano-5-methyl-5-phenylbarbituric acid rem sodium, obtained by condensation of about 1 mol of phenylethylmalonic acid ester with about 1 mol of dicyandiamide in the presence of about 2 moles of sodium methylate,
140 parts of dimethyl sulfate are allowed to run in with stirring, the temperature being kept below 50 during the addition. When the reaction temperature has decreased, the methyl alcohol is distilled off, 6 times its weight of 20% aqueous sulfuric acid are added to the residue and the mixture is refluxed for 6 hours while stirring. After cooling, the 1,5-dimethyl-5-phenylbarbituric acid which has separated out in crystalline form is filtered off with suction and recrystallized from alcohol. Colorless crystals with a melting point of 154 ° are obtained.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE171981X | 1931-12-31 | ||
| CH169179T | 1932-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH171981A true CH171981A (en) | 1934-09-15 |
Family
ID=25718687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH171981D CH171981A (en) | 1931-12-31 | 1932-09-05 | Process for the preparation of a barbituric acid derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH171981A (en) |
-
1932
- 1932-09-05 CH CH171981D patent/CH171981A/en unknown
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