CH166675A - Process for the preparation of an N-alkylated derivative of barbituric acid. - Google Patents

Process for the preparation of an N-alkylated derivative of barbituric acid.

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Publication number
CH166675A
CH166675A CH166675DA CH166675A CH 166675 A CH166675 A CH 166675A CH 166675D A CH166675D A CH 166675DA CH 166675 A CH166675 A CH 166675A
Authority
CH
Switzerland
Prior art keywords
preparation
acid
sub
allyl
condensing agent
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 CH166675A publication Critical patent/CH166675A/en

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Description

  

  Verfahren zur Darstellung eines     N-alkyllerten        Abkömmlings    der     Barbitursäure.       Das Hauptpatent     betrifft    die Darstellung  einer     N-alkylierten        C-disubstituierten        Barbi-          tursäure.     



  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung von     C-Allyl-          C-    (d- 2 . 3 -     cyclopentenyl)-N-methylbarbitur-          säure.    Das Verfahren ist dadurch gekenn  zeichnet, dass man einen     Allyl-(d-2.3-cyclopen-          tenyl)-cyanessigsäureester    mit     Monomethyl-          harnstoff    in Gegenwart eines Kondensations  mittels kondensiert und das entstandene  Zwischenprodukt zur     C-Allyl-C-(d-2.3-cyclo-          pentenyl)-N-methylbai-bitursäure    verseift.  



  Als Kondensationsmittel verwendet man  zweckmässig     Metallalkoholate,    insbesondere  solche der     Alkalimetalle.    Dabei ist es vor  teilhaft als Verdünnungsmittel einen Alkohol  zum Beispiel Äthylalkohol zuzusetzen.  



  Die     Verseifung    geschieht vorteilhaft durch  verdünnte Mineralsäure.  



  Die neue Verbindung, die nach dem Um  kristallisieren aus     Benzol-Petroläther    den    Schmelzpunkt     981'    zeigt, bildet farblose Na  deln. Sie soll therapeutische Verwendung  finden.    <I>Beispiel:</I>  10     gr    Natrium werden in 250     cm3    abso  lutem Alkohol gelöst, dann mit 20     gr        Methyl-          harnstoff    und 44     gr        Allyl-(d-2.3-cyclopen-          tenyl)    -     cyanessigsäureäthylester    10 Stunden  unter     Rückfluss    zum Sieden erhitzt.

   Dann  wird der Alkohol     abdestilliert    und der Rück  stand mit 200     cm3    25     o/oiger    Schwefelsäure  7 Sunden verkocht. Man saugt ab, wäscht  mit Wasser und kristallisiert aus Benzol unter  Zusatz von     Petroläther    um. Man erhält farb  lose Nadeln vom Schmelzpunkt<B>980.</B>



  Process for the preparation of an N-alkylated derivative of barbituric acid. The main patent concerns the preparation of an N-alkylated C-disubstituted barbaric acid.



  The subject of the present patent is a process for the preparation of C-allyl-C- (d- 2. 3 - cyclopentenyl) -N-methylbarbituric acid. The process is characterized in that an allyl (d-2,3-cyclopentenyl) -cyanoacetic acid ester is condensed with monomethyl urea in the presence of a condensation agent and the intermediate product formed is converted to C-allyl-C- (d-2,3-cyclo - pentenyl) -N-methylbai-bituric acid saponified.



  Metal alcoholates, especially those of the alkali metals, are expediently used as the condensing agent. It is advantageous to add an alcohol, for example ethyl alcohol, as a diluent.



  The saponification is advantageously carried out using dilute mineral acid.



  The new compound, which after crystallizing from benzene petroleum ether shows the melting point 981 ', forms colorless needles. It should find therapeutic use. <I> Example: </I> 10 grams of sodium are dissolved in 250 cm3 of absolute alcohol, then with 20 grams of methyl urea and 44 grams of allyl (d-2,3-cyclopentenyl) ethyl cyanoacetate under reflux for 10 hours heated.

   Then the alcohol is distilled off and the residue was boiled for 7 hours with 200 cm3 of 25% sulfuric acid. It is filtered off with suction, washed with water and recrystallized from benzene with the addition of petroleum ether. Colorless needles with a melting point of <B> 980 </B> are obtained

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung der C-Allyl- C - (d - 2. 3-cyclopentenyl) - N - methylbarbitur- säure, dadurch gekennzeichnet, dass man Monomethylharnstoff und Allyl-(d-2.3-cyclo- pentenyl)-epaciessigsäureester in Gegenwart eines Kondensationsmittels kondensiert und das entstandene Zwischenprodukt verseift. Die neue Verbindung, die bei 98 schmilzt, bildet farblose Nadeln und soll therapeutische Verwendung finden. PATENT CLAIM: Process for the preparation of C-allyl C - (d - 2. 3-cyclopentenyl) - N - methylbarbituric acid, characterized in that monomethylurea and allyl (d-2.3-cyclo-pentenyl) epaciacetic acid ester are present in the presence condensed with a condensing agent and saponified the intermediate product formed. The new compound, which melts at 98, forms colorless needles and is believed to have therapeutic uses. UNTERANSPRÜCHE: 1. Verfahren-nach- Patentanspruch, dadurch gekennzeichnet, dass als Kondensations mittel ein Metallalkoholat verwendet wird. 2. Verfahren nach Patentanspruch und Unter anspruch 1, dadurch gekennzeichnet, dass als Kondensationsmittel ein Alkalialko- holat verwendet wird. 3. Verfahren nach Patentanspruch und Unter ansprüchen 1 und 2, dadurch gekennzeich net, dass ein Alkohol als Verdünnungs mittel verwendet wird. 4. Verfahren nach Patentanspruch und Unter anspruch 3, dadurch gekennzeichnet, dass als Kondensationsmittel Natriumalkoholat und als Verdünnungsmittel Athylalkohol Verwendung findet. SUBClaims: 1. Method according to claim, characterized in that a metal alcoholate is used as the condensation agent. 2. The method according to claim and sub-claim 1, characterized in that an alkali alcoholate is used as the condensing agent. 3. The method according to claim and sub-claims 1 and 2, characterized in that an alcohol is used as a diluent. 4. The method according to claim and sub-claim 3, characterized in that sodium alcoholate is used as the condensing agent and ethyl alcohol is used as the diluent. "o. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Verseifung mittelst einer verdünnten Mineralsäure durchführt. "O. The method according to claim, characterized in that the saponification is carried out using a dilute mineral acid.
CH166675D 1931-05-16 1932-05-14 Process for the preparation of an N-alkylated derivative of barbituric acid. CH166675A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE166675X 1931-05-16
CH163696T 1932-05-14

Publications (1)

Publication Number Publication Date
CH166675A true CH166675A (en) 1934-01-15

Family

ID=25717850

Family Applications (1)

Application Number Title Priority Date Filing Date
CH166675D CH166675A (en) 1931-05-16 1932-05-14 Process for the preparation of an N-alkylated derivative of barbituric acid.

Country Status (1)

Country Link
CH (1) CH166675A (en)

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