CH171980A - Process for the preparation of a barbituric acid derivative. - Google Patents

Process for the preparation of a barbituric acid derivative.

Info

Publication number
CH171980A
CH171980A CH171980DA CH171980A CH 171980 A CH171980 A CH 171980A CH 171980D A CH171980D A CH 171980DA CH 171980 A CH171980 A CH 171980A
Authority
CH
Switzerland
Prior art keywords
preparation
acid
sub
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 CH171980A publication Critical patent/CH171980A/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines     Barhitnrsäurederivates.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Darstellung von     1,5-Di-          rrietlryl-5-plierrylbarbitursäure.    Das Verfahren  ist dadurch     gekennzeichnet,    dass man auf 2,4       Diirrrino-3-oyan-5-rnetlryl-5-phenylbarbitur-          säure    ein     Methylierungswittel    einwirken lässt  und das     Methylierungsprodukt    der     Verseifung     unterwirft. Als     Methylierungsmittel    verwen  det     rnan    z.

   B.     Methyljodid,        Dirnetlrylsulfa.t     oder einen aromatischen     SulforrS.!Llrenrethyl-          ester    in     (xegenwar,t    von Alkali,     zweekmässig          Alkalialkoholat.    Die Reaktion wird normaler  weise in     Gegenwart    eines Löse- oder     Ver-          dünneinittelsausgeführt.        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 farblose     Kristalle     vom Schmelzpunkt 154o. Es ist in Wasser       praktisch    unlöslich; löst sich aber in wässe  rigen     Alkalien.    Es soll therapeutische Anwen  dung     finden.       <I>Beispiel:

  </I>  46 Teile Natrium löst man in 300 Teilen  Methanol, gibt hierzu 92 Teile     Dicyandiamid     und 203 Teile     Pherrylmethylayairessigsäure-          äthylester        (Kpis    145 ) und erhitzt etwa 10       Stunden    auf<B>70-80'</B> am     Rückflusskühler.    Zu  der erkalteten, die     2,4-Diirnirro-3-cyan-5-rrre-          thyl-5-plierrylbai,bitrrrsäure    enthaltenden Lö  sung fügt man hierauf 240 Teile     Dimethyl-          sulfat,    wobei man dafür Sorge trägt, dass die  Temperatur nicht über 50   steigt.

   Nach mehr  stündigem Stehen destilliert man das     Metha-          r)ol    im     Vakuum    ab und verkocht den Rück  stand mit dem Sechsfachen seines Gewichtes  25      /oiger    Schwefelsäure. Nach dem     Erkalten     saugt man das abgeschiedene     Kristallmehl    ab  und löst aus     kochendem    Wasser um. Die so  gewonnene     1,5-Dimethyl-5-phenylbarbitur-          säure    bildet farblose Nadeln vom F. 154".



  Process for the preparation of a barhydric acid derivative. The subject of the present patent is a process for the preparation of 1,5-dirrietlryl-5-plierrylbarbituric acid. The process is characterized in that a methylation agent is allowed to act on 2,4 diirrrino-3-oyan-5-methyl-5-phenylbarbituric acid and the methylation product is subjected to saponification. The methylating agent used is e.g.

   B. methyl iodide, dirnetyl sulfa, or an aromatic sulphur.! Lrenrethyl ester in (xegenwar, t of alkali, two-fold alkali alcoholate. The reaction is usually carried out in the presence of a solvent or thinning agent. Alcohols are expediently used for this Saponification agents are preferably dilute mineral acids.



  The new product obtained in the manner described forms colorless crystals with a melting point of 154o. It is practically insoluble in water; but dissolves in aqueous alkalis. It should find therapeutic use. <I> example:

  46 parts of sodium are dissolved in 300 parts of methanol, 92 parts of dicyandiamide and 203 parts of Pherrylmethylayaeaessigsäure- ethyl ester (Kpis 145) are added and the mixture is heated to 70-80 'on the reflux condenser for about 10 hours. 240 parts of dimethyl sulphate are then added to the solution containing 2,4-diirirro-3-cyano-5-rrrrethyl-5-plierrylbai, biturric acid, taking care that the temperature does not exceed 50% increases.

   After standing for more hours, the methanol is distilled off in vacuo and the residue is boiled off with six times its weight of 25% sulfuric acid. After cooling down, the separated crystal flour is sucked off and dissolved in boiling water. The 1,5-dimethyl-5-phenylbarbituric acid obtained in this way forms colorless needles of 154 ".

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Darstellung von 1,5-Di- methyl-5-phenylbarbitLrrsäure, dadurch ge- kennzeichnet, dass man auf 2,4-Diimirio-3- cyan-5-methyl-5-phenylbarbitui,säur-e ein Me- thylierungsmittel einwirken lässt und das Methylierungsprodukt der Verseifung unter wirft. Die so erhältliche, bisher noch nicht be kannte 1,5-Diinethyl-5-plietiylbarbitursäui@e bildet farblose Kristalle vom F. 1540, die in wässerigen Alkalien löslich sind. UNTERANSPRüCHE: 1. <B> PATENT CLAIM: </B> Process for the preparation of 1,5-dimethyl-5-phenylbarbital acid, characterized in that 2,4-diimirio-3-cyano-5-methyl-5-phenylbarbitui , acid-e allows a methylating agent to act and subjects the methylation product to saponification. The 1,5-Diinethyl-5-Plietiylbarbitursäui @ e, which is available in this way and was previously unknown, forms colorless crystals of F. 1540, which are soluble in aqueous alkalis. SUBCLAIMS: 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass als Methylierungsmit- tel Diinethylsiilfat in Gegenwart von Al kali Verwendung findet. 2. Verfahren nach Patentanspruch und Unter anspruch 1, dadurch gekennzeichnet, dass in Gegenwart eines Verdünnemittels gear beitet wird. 3. Verfahren nach Patentanspruch und Unter- anSpruch 2, dadurch gekennzeichnet, dass Alkohol als Verdünnemittel Verwendung findet. 4. Process according to patent claim, characterized in that diinethylsilfate is used as the methylating agent in the presence of alkali. 2. The method according to claim and sub-claim 1, characterized in that gear is processed in the presence of a diluent. 3. The method according to claim and sub- to claim 2, characterized in that alcohol is used as a diluent. 4th Verfahren nach Patentanspruch und Unter ansprüchen 1-3, dadurch gekennzeichnet, dass verdünnte Mineralsäuren als Versei fungsmittel zur Anwendung kommen. Method according to patent claim and sub-claims 1-3, characterized in that dilute mineral acids are used as saponifying agents.
CH171980D 1931-12-31 1932-09-05 Process for the preparation of a barbituric acid derivative. CH171980A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE171980X 1931-12-31
CH169179T 1932-09-05

Publications (1)

Publication Number Publication Date
CH171980A true CH171980A (en) 1934-09-15

Family

ID=25718686

Family Applications (1)

Application Number Title Priority Date Filing Date
CH171980D CH171980A (en) 1931-12-31 1932-09-05 Process for the preparation of a barbituric acid derivative.

Country Status (1)

Country Link
CH (1) CH171980A (en)

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