CH127177A - Process for the preparation of isopropylisopropenylpropargylbarbituric acid. - Google Patents

Process for the preparation of isopropylisopropenylpropargylbarbituric acid.

Info

Publication number
CH127177A
CH127177A CH127177DA CH127177A CH 127177 A CH127177 A CH 127177A CH 127177D A CH127177D A CH 127177DA CH 127177 A CH127177 A CH 127177A
Authority
CH
Switzerland
Prior art keywords
acid
isopropylisopropenylpropargylbarbituric
preparation
ether
alcohol
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 CH127177A publication Critical patent/CH127177A/en

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung von     Isopropylisopropenylpropargylbarbitursäure.       Gegenstand dieses Patentes ist ein Ver  fahren zur Darstellung der     Isopropylisopro-          penylpropargylbarbitursäure,    welches dadurch  gekennzeichnet ist, dass man auf ein Alkali  salz der     Monoisopropylbarbitursäure    ein     Iso-          propenylpropargylhalogenid,    welchem die all  gemeine Formel  
EMI0001.0007     
    zukommt, einwirken lässt.  



  Die     Isopropylisopropenylpropargylbarbitur-          säure    welche in der Therapie als Schlaf- und       Beruhigungsmittel    Verwendung finden soll,  besitzt einen Schmelzpunkt von 157 0 und  löst sich leicht in     Alkalien,    Äther und Al  kohol und ist schwer löslich in Wasser. Die  Verbindung entfärbt     Permanganat    augen  blicklich.  



       Beispiel:     41     gr        Isopropylbarbitursäure    werden in       der        berechneten        Menge    5     %        Natronlauge        ge-          löst    und 39     gr        Isopropenylpropargylbromid     in 160     cm3    Alkohol zugesetzt. Man lässt 10    Stunden bei Zimmertemperatur stehen und  erwärmt dann 10 Stunden auf 50 0.

   Nach  dem     Abdestillieren    des Alkohols im Vakuum       hinterbleibt    die     Isopropyl-isopropenylpropar-          gylbarbitursäure    als fester Kuchen. Nach dem       Ümlösen    aus Sprit zeigt sie den F. P. 157 0.  Die Verbindung entfärbt     Permanganat    augen  blicklich. Das Produkt löst sich leicht in  Alkalien, Äther und Alkohol und ist schwer  löslich in Wasser.  



  Das     Isopropenylpropargylbromidkann    man  auf folgende Weise gewinnen  Zu einer     Grignardlösung    von 40     gr        Xag-          nesium,    210     gr    Bromäthyl und 500     cm0    Äther,  lässt man unter Eiskühlung 120     gr        Isopro-          penylacetylen    (gewonnen aus     Methylbutinol     durch Wasserabspaltung) in 90 cm-' Äther       zutropfen.    Nach zwei Stunden wird die Eis  kühlung weggenommen,

   sechs Stunden bei  Zimmertemperatur und zuletzt eine Stunde  unter     Rückfluss    gerührt. Man kühlt nun wie  der stark ab, und leitet unter Rühren und       Rückfluss    in die Ätherlösung des     Isopropenyl-          propargy1magnesiumbromids    Formaldehyd ein,  der aus<B>85</B> kg absolut trockenem Paraformal-           dehyd    durch Erhitzen     gewonn(3n    wird. Nach  dem Zersetzen mit Wasser und     Ansäuren     mit verdünnter Schwefelsäure wird die äthe  rische Schicht abgetrennt und über Pottasche  getrocknet.

   Nach dem     Abdestillieren    des  Äthers siedet der     Isopropenylpropargylalkohol     bei     11    mm bei 68-69  . 30     gr    des so ge  wonnenen Alkohols werden mit 100     gr        AZe-          thylenchlorid    versetzt und unter Rühren und  starkem     Kühlen    28,2     gr        Phosphortribromid     eingetropft.

   Nach zwei Stunden wird mit  Eiswasser geschüttelt und nach dem     Abdestil-          lieren    des     Methylenchlorids    das     Isopropenyl-          propargylbromid    vom Schmelzpunkt<B>65-670</B>  bei 20 mm gewonnen.



  Process for the preparation of isopropylisopropenylpropargylbarbituric acid. The subject of this patent is a method for the preparation of isopropylisopropylpropargylbarbituric acid, which is characterized in that an isopropenylpropargylhalide, which has the general formula, is added to an alkali salt of monoisopropylbarbituric acid
EMI0001.0007
    comes to, lets act.



  Isopropylisopropenylpropargylbarbituric acid, which is supposed to be used in therapy as a sleeping and sedative, has a melting point of 157 ° and is easily soluble in alkalis, ether and alcohol and is sparingly soluble in water. The compound discolors permanganate instantly.



       Example: 41 grams of isopropylbarbituric acid are dissolved in the calculated amount of 5% sodium hydroxide solution and 39 grams of isopropenylpropargyl bromide are added in 160 cm3 of alcohol. The mixture is left to stand for 10 hours at room temperature and then heated to 50 ° for 10 hours.

   After the alcohol has been distilled off in vacuo, the isopropylisopropenylpropargylbarbituric acid remains as a solid cake. After dissolving from fuel it shows the F. P. 157 0. The connection discolor permanganate instantly. The product dissolves easily in alkalis, ether and alcohol and is sparingly soluble in water.



  The isopropenylpropargyl bromide can be obtained in the following way. To a Grignard solution of 40 g xagnesium, 210 g bromoethyl and 500 cm0 ether, 120 g isopropyl acetylene (obtained from methylbutynol by elimination of water) in 90 cm ether is added dropwise while cooling with ice. After two hours the ice cooling is removed,

   Stirred for six hours at room temperature and finally one hour under reflux. The mixture is then cooled down strongly and, with stirring and reflux, formaldehyde is introduced into the ether solution of the isopropenyl propargyl magnesium bromide, which is obtained from 85 kg of absolutely dry paraformaldehyde by heating (3n. After decomposition the ethereal layer is separated using water and acidic acid with dilute sulfuric acid and dried over potash.

   After the ether has been distilled off, the isopropenylpropargyl alcohol boils at 11 mm at 68-69. 30 g of the alcohol thus obtained are mixed with 100 g of acetylene chloride and 28.2 g of phosphorus tribromide are added dropwise with stirring and vigorous cooling.

   After two hours, it is shaken with ice water and, after the methylene chloride has been distilled off, the isopropenylpropargyl bromide with a melting point of 65-670 at 20 mm is obtained.

Claims (1)

<B>PATENTANSPRUCH</B> Verfahren zur Darstellung von Isopropyl- isopropenylpropargylbarbitursäure, dadurch ge- kennzeichnet, üag man auf ein Alkalisalz der Monoisopropylbarbitursäure ein Isoprope- nylpropargy1halogenid der folgenden Formel: EMI0002.0026 einwirken lässt. <B> PATENT CLAIM </B> Process for the preparation of isopropylisopropenylpropargylbarbituric acid, characterized in that an isopropylpropenylpropargyl halide of the following formula is added to an alkali salt of monoisopropylbarbituric acid: EMI0002.0026 can act. Die Isopropylisopropenylpropargylbarbitur- säure, welche in der Therapie als Schlaf- und Beruhigungsmittel Verwendung finden soll, schmilzt bei 157 , sie löst sich leicht in Alkalien, Äther und Alkohol und ist schwer löslich in Wasser, Permanganat wird von der Verbindung augenblicklich entfärbt. Isopropylisopropenylpropargylbarbituric acid, which is said to be used in therapy as a sleeping and sedative, melts at 157, it dissolves easily in alkalis, ether and alcohol and is sparingly soluble in water. Permanganate is instantly discolored by the compound.
CH127177D 1926-12-13 1926-12-13 Process for the preparation of isopropylisopropenylpropargylbarbituric acid. CH127177A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH127177T 1926-12-13
CH124869T 1926-12-13

Publications (1)

Publication Number Publication Date
CH127177A true CH127177A (en) 1928-08-16

Family

ID=25710369

Family Applications (1)

Application Number Title Priority Date Filing Date
CH127177D CH127177A (en) 1926-12-13 1926-12-13 Process for the preparation of isopropylisopropenylpropargylbarbituric acid.

Country Status (1)

Country Link
CH (1) CH127177A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2872448A (en) * 1959-02-03 S-trisubstituted barbituric acids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2872448A (en) * 1959-02-03 S-trisubstituted barbituric acids

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