CH171981A - Process for the preparation of a barbituric acid derivative. - Google Patents

Process for the preparation of a barbituric acid derivative.

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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
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH171981A publication Critical patent/CH171981A/en

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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)

PATENTANSPRUCH: Verfahren zur Darstellung von 1,5-Dime- thyl-5-phenylbarbitursäure, dadurch gekenn- zeichnet, dass man auf 2-Imiiio-3-cyan-5-me- thyl-5-phenylbarbitursäure ein Methylierungs- mittel einwirken lässt und das Methylierungs- produkt der Verseifung unterwirft. Die so erhältliche, bisher noch nicht be kannte 1,5-Dimethyl-5-phenylbarbitursätire bildet farblose Kristalle vom F. 154 , die in wässerigen Alkalien löslich sind. UNTERANSPRACHE: 1. PATENT CLAIM: Process for the preparation of 1,5-dimethyl-5-phenylbarbituric acid, characterized in that a methylating agent is allowed to act on 2-imiiio-3-cyano-5-methyl-5-phenylbarbituric acid and subjects the methylation product to saponification. The 1,5-dimethyl-5-phenylbarbiturates obtainable in this way, not previously known, forms colorless crystals of F. 154, which are soluble in aqueous alkalis. SUB-TALK: 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass als Methylierungs- mittel Dimethylsulfat in Gegenwart von Alkali Verwendung findet. 2. Verfahren nach Patentanspruch und Unter anspruch 1, dadurch gekennzeichnet, dass in Gegenwart eines Verdünnemittels ge arbeitet wird. 3. Verfahren nach Patentanspruch und Unter anspruch 2, dadurch gekennzeichnet, dass Alkohol als Verdünnemittel Verwendung findet. 4. Verfahren nach Patentanspruch und Unter ansprüchen 1-3, dadurch gekennzeichnet, dass verdünnte Mineralsäuren als Versei fungsmittel zur Anwendung kommen. Process according to patent claim, characterized in that dimethyl sulfate is used as the methylating agent in the presence of alkali. 2. The method according to claim and sub-claim 1, characterized in that ge works in the presence of a diluent. 3. The method according to claim and sub-claim 2, characterized in that alcohol is used as a diluent. 4. The method according to claim and sub-claims 1-3, characterized in that dilute mineral acids are used as saponifying agents.
CH171981D 1931-12-31 1932-09-05 Process for the preparation of a barbituric acid derivative. CH171981A (en)

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)

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