CH244952A - Process for the preparation of an acylated, aliphatic aminocarboxamide. - Google Patents

Process for the preparation of an acylated, aliphatic aminocarboxamide.

Info

Publication number
CH244952A
CH244952A CH244952DA CH244952A CH 244952 A CH244952 A CH 244952A CH 244952D A CH244952D A CH 244952DA CH 244952 A CH244952 A CH 244952A
Authority
CH
Switzerland
Prior art keywords
aminocarboxamide
acylated
aliphatic
preparation
butyric acid
Prior art date
Application number
Other languages
German (de)
Inventor
Ag J R Geigy
Original Assignee
Ag J R Geigy
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 Ag J R Geigy filed Critical Ag J R Geigy
Publication of CH244952A publication Critical patent/CH244952A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung eines     acylierten,        aliphatischen        Aminocarbonsäureamids.       Gegenstand des vorliegenden     Patentes    ist       ein    Verfahren zur Darstellung eines     acylier-          ten,        aliphatischen        Aminocarbonsäureamids.     Das Verfahren ist dadurch gekennzeichnet,  dass     N-Crotonyl-a-amino-n-buttersäuredime-          thylamid        äthyliert    wird.  



       Dass        N-C'rotonyl-a-äthylamino-n-butter-          säuredimethylamid    der Formel         CH3-CHZ-CH-CO-N(CH3)2          CH3-CHZ-N-CO-CH=CH-CH3       bildet     eine    fast farblose Flüssigkeit vom       Siedepunkt    162 bis 134  unter 0,06     mm.    Die  neue Verbindung soll     therapeutische    Verwen  dung     finden.     



  <I>Beispiel:</I>  26 Teile     a-Amino-n-buttersäuredimethyl-          amid    werden     in.    200 Teilen Äther gelöst und  unter Rühren und Kühlen 10;4 Teile     Croton-          säurechlorid        zugetropft.    Nach zweistündigem  Rühren wird vom     a-Amino-n-buttersäure-          dimethylamid-chlorhydrat    filtriert, vom    Äther durch Destillation befreit und das Pro  dukt fraktioniert:

   Siedepunkt 170 bis 172   unter 0,2     mm.    20 Teile des erhaltenen       N-Crotonylamino-n-buttersäuredimethylamids     in 200 Teilen     Xylol    werden mit 4 Teilen       Natriumamid        einige    Zeit zum Sieden erhitzt.  Nach dem     Abkühlen    wird mit 32 Teilen       Äthyljodid    versetzt und im Druckgefäss auf  150 bis 160  erhitzt.

   Das Reaktionsprodukt  wird mit     gesättigter    Kalilauge durchgeschüt  telt und die     Xylollösung        abgetrennt.    Nach  dem     Abdestillieren    des     Xylols        wird    der Rück  stand     im    Hochvakuum rektifiziert. Die neue  Verbindung zeigt den     .Siedepunkt    132 bis  134  unter 0,03 mm und ist leicht löslich     in     Wasser und     organischen        Lösungsmitteln.  



  Process for the preparation of an acylated, aliphatic aminocarboxamide. The present patent relates to a process for the preparation of an acylated, aliphatic aminocarboxamide. The process is characterized in that N-crotonyl-a-amino-n-butyric acid dimethylamide is ethylated.



       The N-C'rotonyl-a-äthylamino-n-butyric acid dimethylamide of the formula CH3-CHZ-CH-CO-N (CH3) 2 CH3-CHZ-N-CO-CH = CH-CH3 forms an almost colorless liquid from Boiling point 162 to 134 below 0.06 mm. The new compound is intended to find therapeutic use.



  <I> Example: </I> 26 parts of a-amino-n-butyric acid dimethyl amide are dissolved in 200 parts of ether and 10.4 parts of crotonic acid chloride are added dropwise with stirring and cooling. After stirring for two hours, the a-amino-n-butyric acid dimethylamide chlorohydrate is filtered, the ether is removed by distillation and the product is fractionated:

   Boiling point 170 to 172 below 0.2 mm. 20 parts of the resulting N-crotonylamino-n-butyric acid dimethylamide in 200 parts of xylene are heated to the boil for some time with 4 parts of sodium amide. After cooling, 32 parts of ethyl iodide are added and the mixture is heated to 150 to 160 in a pressure vessel.

   The reaction product is shaken through with saturated potassium hydroxide solution and the xylene solution is separated off. After the xylene has been distilled off, the residue is rectified in a high vacuum. The new compound shows the boiling point 132 to 134 below 0.03 mm and is easily soluble in water and organic solvents.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines acylier- ten, aliphatischen Aminocarbonsäureamids, dadurch gekennzeichnet, dass N-Crotonyl-a- amino-n-buttersäuredimethylamid äthyliert wird. Das N-Crotonyl-a-äthylamino-n-butter- säuredimethylamid der Formel EMI0002.0003 bildet eine fast farblose Flüssigkeit vom Siedepunkt 132 bis 134 unter 0,03 mm. Die neue Verbindung soll therapeutische Verwendung finden. PATENT CLAIM: Process for the preparation of an acylated, aliphatic aminocarboxamide, characterized in that N-crotonyl-a-amino-n-butyric acid dimethylamide is ethylated. The N-crotonyl-a-ethylamino-n-butyric acid dimethylamide of the formula EMI0002.0003 forms an almost colorless liquid with a boiling point of 132 to 134 below 0.03 mm. The new compound should find therapeutic use.
CH244952D 1942-12-18 1942-12-18 Process for the preparation of an acylated, aliphatic aminocarboxamide. CH244952A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH244952T 1942-12-18

Publications (1)

Publication Number Publication Date
CH244952A true CH244952A (en) 1946-10-15

Family

ID=4464599

Family Applications (1)

Application Number Title Priority Date Filing Date
CH244952D CH244952A (en) 1942-12-18 1942-12-18 Process for the preparation of an acylated, aliphatic aminocarboxamide.

Country Status (1)

Country Link
CH (1) CH244952A (en)

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