CH116524A - Process for the preparation of a derivative of barbituric acid. - Google Patents

Process for the preparation of a derivative of barbituric acid.

Info

Publication number
CH116524A
CH116524A CH116524DA CH116524A CH 116524 A CH116524 A CH 116524A CH 116524D A CH116524D A CH 116524DA CH 116524 A CH116524 A CH 116524A
Authority
CH
Switzerland
Prior art keywords
preparation
acid
derivative
barbituric acid
isopropylbarbituric
Prior art date
Application number
Other languages
German (de)
Inventor
J. D. Riedel Aktiengesellschaft
Original Assignee
Riedel J D 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 Riedel J D Ag filed Critical Riedel J D Ag
Publication of CH116524A publication Critical patent/CH116524A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Saccharide Compounds (AREA)

Description

       

  Verfahren zur Darstellung eines Derivate, der     Barbitur,äure.            Im.    Hauptpatent wurde     gezeigt,    dass  solche an der     Methylengruppe    substituierte       Barbitursäuren,    bei welchen mindestens ein       Methylenwasserstoffatom    durch einen     ss-Bro-          mallylrest    ersetzt ist, ausgezeichnet wirk  same Schlafmittel vorstellen.

   In weiterer  Entwicklung des Verfahrens des Haupt  patentes wurde gefunden, dass überraschen  derweise der     ss-Chlorallylrest    die Wirksam  keit der     Barbitursäuren        ebenfalls    äusserst  günstig beeinflusst.  



  Die Darstellung der neuen Verbindung  geschieht analog dem im Hauptpatent be  schriebenen Verfahren, indem man an Stelle  des     1.2-Dibrom-2.3-propylens        bezw.    des       Tribrompropans    1     Halogen-2-Chlor-2.        3-pro-          pylen    von der Formel     CH-        (Hlg)-CCl    =     CHZ     (wobei     Hlg    Chlor oder Brom bedeutet)  auf     Isopropylbarbitursäure    zur     Einwirkung     bringt.

      <I>Beispiel</I>  170 Gewichtsteile     Isopropylbarbitursäure     werden in 500 Volumenteilen zweifach nor  mal Natronlauge gelöst und nach Zusatz von  125 Gewichtsteilen 1.2-Dichlor-2.3-pro-         pylen    mehrere Stunden bei lebhaftem Rühren  unter     Rückfluss    erwärmt. Nach beendeter  Einwirkung wird das ausgeschiedene Reak  tionsprodukt abgesaugt und aus wässerigem  Alkohol umkristallisiert. Es wird in langen  farblosen, filzigen Nadeln vom     Fp.   <B>171</B>   er  halten und stellt, wie die     Anlayse    ergibt,  die     ss-Monochlorallyl-isopropylbarbitursäure     vor.  



  Dieses     Barbitursäurederivat    ist in Alko  hol, Äther und Aceton leicht löslich, in  Chloroform,     Tetralin    und Wasser schwer  löslich. Es wird von verdünnter     Sodalösung     und Natronlauge leicht aufgenommen und  mit Säuren aus seiner alkalischen Lösung un  verändert     abgeschieden.     



  Zum gleichen Produkt kommt man,     wenn          2-Chlor-3-brompropen-(1)    unter denselben  Reaktionsbedingungen auf das     Natriumsalz     der     Isopropylbarbitursäure    einwirken lässt.



  Process for the preparation of a derivative, the barbituric acid. In the main patent it was shown that those barbituric acids substituted on the methylene group, in which at least one methylene hydrogen atom has been replaced by an β-bromallyl radical, present excellently effective sleeping pills.

   In a further development of the process of the main patent, it was found that, surprisingly, the ß-chlorallyl radical also has an extremely beneficial effect on the effectiveness of the barbituric acids.



  The presentation of the new compound is done analogously to the process described in the main patent by BEZW instead of 1.2-dibromo-2.3-propylene. of tribromopropane 1 halogen-2-chloro-2. 3-propylene of the formula CH- (Hlg) -CCl = CHZ (where Hlg denotes chlorine or bromine) acts on isopropylbarbituric acid.

      <I> Example </I> 170 parts by weight of isopropylbarbituric acid are dissolved twice normal sodium hydroxide solution in 500 parts by volume and, after addition of 125 parts by weight of 1,2-dichloro-2,3-propylene, heated under reflux for several hours with vigorous stirring. After the action has ended, the precipitated reaction product is filtered off with suction and recrystallized from aqueous alcohol. It is obtained in long, colorless, felt-like needles with a melting point of <B> 171 </B> and, as the analysis shows, it represents ß-monochloroallyl-isopropylbarbituric acid.



  This barbituric acid derivative is easily soluble in alcohol, ether and acetone, and sparingly soluble in chloroform, tetralin and water. It is easily absorbed by dilute soda solution and sodium hydroxide solution and separated from its alkaline solution with acids without any changes.



  The same product is obtained if 2-chloro-3-bromopropene (1) is allowed to act on the sodium salt of isopropylbarbituric acid under the same reaction conditions.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines schlaf machenden Derivates der Barbitursäure, da durch gekennzeichnet, dass man Isopropylbar- bitursäure mit 1-Halogen-2-Chlor-2. ä-pro- pj len umsetzt. PATENT CLAIM: Process for the preparation of a sleep-inducing derivative of barbituric acid, characterized in that isopropylbarbituric acid is mixed with 1-halogen-2-chloro-2. ä-propj len implements. Das erhaltene Produkt kann aus ivässe- rigem Alkohol umkristallisiert werden, wo bei es in langen farblosen, filzigen Nadeln vom Schmelzpunkt 171 erhalten wird; in Al kohol, Äther und Aceton ist es leicht löslich, in Chloroform, Tetraliii und Wasser schwer löslich; von verdünnter Sodalösung und Na tronlauge wird es leicht aufgenommen und mit Säuren aus alkalischer Lösung unverän dert abgeschieden. Das neue Produkt ist die ,8-Monochlorallyl-isopropylbarbitursäure. The product obtained can be recrystallized from aqueous alcohol, where it is obtained in long, colorless, felt-like needles with a melting point of 171; it is easily soluble in alcohol, ether and acetone, but sparingly soluble in chloroform, tetrali and water; it is easily absorbed by dilute soda solution and sodium hydroxide solution and deposited unchanged from alkaline solution with acids. The new product is 8-monochloroallyl-isopropylbarbituric acid.
CH116524D 1924-09-19 1924-09-19 Process for the preparation of a derivative of barbituric acid. CH116524A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH111883T 1924-09-19
CH116524T 1924-09-19

Publications (1)

Publication Number Publication Date
CH116524A true CH116524A (en) 1926-09-01

Family

ID=25707949

Family Applications (1)

Application Number Title Priority Date Filing Date
CH116524D CH116524A (en) 1924-09-19 1924-09-19 Process for the preparation of a derivative of barbituric acid.

Country Status (1)

Country Link
CH (1) CH116524A (en)

Similar Documents

Publication Publication Date Title
CH116524A (en) Process for the preparation of a derivative of barbituric acid.
DE1198831B (en) Process for the preparation of 3-aralkylsalicylic acids
DE872947C (en) Process for the production of basic ethers, thioether and their salts
AT102313B (en) Process for the representation of complex gold compounds.
AT137670B (en) Process for the representation of organic mercury bonds.
AT120852B (en) Process for the preparation of C, C-disubstituted barbituric acids.
AT105086B (en) Process for the preparation of N-methylsulphurous acid salts of secondary, aromatic-aliphatic amines.
AT153203B (en) Process for the preparation of water-soluble mercury compounds.
DE249726C (en)
DE188435C (en)
AT157720B (en) Process for the production of glucosides.
DE485832C (en) Process for the preparation of C, C-disubstituted derivatives of barbituric acid
DE513205C (en) Process for the preparation of derivatives of the aminoarylantimony compounds
AT131127B (en) Process for the preparation of salts of iodomethanesulfonic acid or its homologues.
DE193542C (en)
DE531222C (en) Process for the preparation of bismuth dithioglycolic acid and its salts
CH124870A (en) Process for the preparation of 1-aurothioglucose.
CH121259A (en) Process for the preparation of an acyl compound of amino-3-chloro-4-oxybenzene-1-arsic acid.
DEP0019118DA (en) Process for the production of a novel derivative of alpha; -phenylethyl alcohol.
CH262798A (en) Process for the preparation of a new pyrimidyl mercaptocarboxylic acid.
CH116690A (en) Process for the preparation of allyl crotonyl barbituric acid.
CH105106A (en) Process for the preparation of an alkoxyakridine.
CH154175A (en) Process for the preparation of a water-soluble complex salt.
CH210972A (en) Process for the preparation of a urea derivative.
CH210973A (en) Process for the preparation of a urea derivative.