CH124869A - Process for the preparation of isopropylpropargylbarbituric acid. - Google Patents

Process for the preparation of isopropylpropargylbarbituric acid.

Info

Publication number
CH124869A
CH124869A CH124869DA CH124869A CH 124869 A CH124869 A CH 124869A CH 124869D A CH124869D A CH 124869DA CH 124869 A CH124869 A CH 124869A
Authority
CH
Switzerland
Prior art keywords
acid
isopropylpropargylbarbituric
preparation
alcohol
isopropyl
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 CH124869A publication Critical patent/CH124869A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms
    • C07D239/62—Barbituric acids

Description

  

  Verfahren zur Darstellung von     Isopropylpropargylbarbitursäure.       Es     wurde    die Beobachtung gemacht, dass  man zu ausgezeichneten, schlafmachenden  Verbindungen gelangt, wenn man in C. C  Dialhylbarbitursäuren die     Alkylgruppen     teilweise oder ganz durch     Alkingruppen    er  setzt.  



  Die vorliegende Erfindung betrifft ein  Verfahren zur Darstellung der     Isopropylpro-          pargylbarbitursäure,    welches dadurch ge  kennzeichnet ist, dass man auf die     Alkaliver-          bindung    der     Monoisopropylbarbitursäure    ein       Propargylhalogenid    einwirken lässt.  



  Die     Isopropylpropargylbarbitursäure    ist  eine farblose Substanz vom     Schmelzpunkt     16,5   und löst sich leicht in Äther, Alkohol  und heissem Wasser. Ferner ist sie in     Alkä-          lien    leicht löslich.  



  Die Verbindung     entfärbt        Permanganat     augenblicklich.  



       Beispiel:     17     gr        Monoisopropylbarbitursäure    werden  in 11,3     gr    konzentrierter Natronlauge von  35 % Gehalt und 60     gr    50     %igem    Alkohol ge  löst, darauf werden 12     gr        3-Brompropin    zu  gefügt und das Ganze 5 Stunden gekocht.    Dann wird der Alkohol     abdestilliert    und der  Rückstand mit Wasser versetzt. Die ausge  schiedene     Isopropylpropargylbarbitursäure          wird    abgesaugt, gewaschen und aus Wasser  umkristallisiert.

   Die Substanz schmilzt bei  <B>165</B>   und ist leicht löslich in Äther, Alkohol  und heissem Wasser.     Permanganat    wird von  der Verbindung augenblicklich entfärbt.



  Process for the preparation of isopropylpropargylbarbituric acid. It has been observed that excellent, sleep-inducing compounds are obtained if the alkyl groups in C.C. C dialhylbarbituric acids are partially or completely replaced by alkyne groups.



  The present invention relates to a method for the preparation of isopropylpropargylbarbituric acid, which is characterized in that a propargyl halide is allowed to act on the alkali compound of monoisopropylbarbituric acid.



  Isopropylpropargylbarbituric acid is a colorless substance with a melting point of 16.5 and dissolves easily in ether, alcohol and hot water. It is also easily soluble in alkalis.



  The compound discolors permanganate instantly.



       Example: 17 grams of monoisopropylbarbituric acid are dissolved in 11.3 grams of concentrated sodium hydroxide solution of 35% content and 60 grams of 50% alcohol, then 12 grams of 3-bromopropine are added and the whole thing boiled for 5 hours. The alcohol is then distilled off and water is added to the residue. The separated isopropylpropargylbarbituric acid is filtered off with suction, washed and recrystallized from water.

   The substance melts at <B> 165 </B> and is easily soluble in ether, alcohol and hot water. Permanganate is instantly discolored by the compound.

Claims (1)

PATENTANSPRÜCR: Verfahren zur Darstellung von Isopropyl- propargylbarbitursäure, dadurch gekenn zeichnet, dass man auf die Alkaliverbindung der Mono-isopropylbarbitursäure ein Propar- gylhalogenid einwirken lässt. Die Isopropylpropargylbarbitursäure ist eine farblose Substanz, die bei 165 schmilzt, in Äther, Alkohol und heissem Wasser und ferner in Alkalien leicht löslich ist. Perman- ganat wird von der Verbindung augenblick lich entfärbt. PATENT APPLICATION: Process for the preparation of isopropyl propargyl barbituric acid, characterized in that a propargyl halide is allowed to act on the alkali compound of mono-isopropyl barbituric acid. Isopropylpropargylbarbituric acid is a colorless substance, which melts at 165, is easily soluble in ether, alcohol and hot water, and also in alkalis. Permanent is instantly discolored by the connection.
CH124869D 1926-12-13 1926-12-13 Process for the preparation of isopropylpropargylbarbituric acid. CH124869A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH124869T 1926-12-13

Publications (1)

Publication Number Publication Date
CH124869A true CH124869A (en) 1928-03-01

Family

ID=4383463

Family Applications (1)

Application Number Title Priority Date Filing Date
CH124869D CH124869A (en) 1926-12-13 1926-12-13 Process for the preparation of isopropylpropargylbarbituric acid.

Country Status (1)

Country Link
CH (1) CH124869A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2872448A (en) * 1959-02-03 S-trisubstituted barbituric acids
US3185193A (en) * 1964-02-12 1965-05-25 Marion B Orr Hacksaw blade holder

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2872448A (en) * 1959-02-03 S-trisubstituted barbituric acids
US3185193A (en) * 1964-02-12 1965-05-25 Marion B Orr Hacksaw blade holder

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