CH185280A - Process for the preparation of the diethylamide of 3,5-dimethylisoxazole-4-carboxylic acid. - Google Patents

Process for the preparation of the diethylamide of 3,5-dimethylisoxazole-4-carboxylic acid.

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Publication number
CH185280A
CH185280A CH185280DA CH185280A CH 185280 A CH185280 A CH 185280A CH 185280D A CH185280D A CH 185280DA CH 185280 A CH185280 A CH 185280A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
dimethylisoxazole
diethylamide
preparation
ether
Prior art date
Application number
Other languages
German (de)
Inventor
Hoffmann-La Roche & Co. Aktiengesellschaft F.
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Priority to CH190641D priority Critical patent/CH190641A/en
Publication of CH185280A publication Critical patent/CH185280A/en

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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Description

       

  Verfahren zur Darstellung des     Diäthylamids    der     3,6-Dimethylisogazol-4-carbonsäure.       Praktisch     verwertbare    Vertreter der     Isox-          azolreihe    sind bisher noch nicht bekannt ge  worden (vergleiche zum Beispiel     Meyer-          Jacobson,    Lehrbuch der organischen Chemie,       Bd.        II,    dritter Teil,     ;S.    507, letzter Ab  schnitt).

   Es wurde nun gefunden, dass     di-          alkylsubstituierte        Amide    von     Isoxazolcarbon-          säuren        wertvolle    therapeutische Eigenschaf  ten aufweisen. Zur Herstellung dieser     Amide     werden Verbindungen der allgemeinen Formel  
EMI0001.0018     
    führt und diese mit sekundären Aminen um  gesetzt.  



  Gegenstand des vorliegenden     Patentes    ist  ein Verfahren zur Darstellung des     Diäthyl-          amids    der     3,5-Dimethylisogazol-4-carbon-          säure,    welches dadurch gekennzeichnet ist,  dass man     3,5-Dimethylisogazol-4-carbonsäure,     ein Kondensationsmittel und     Diäthylamin     aufeinander einwirken lässt.  



  Das neue     Diäthylamid    der     3,5-Dimethyl-          isogazol-4-carbonsäure    schmilzt bei 24   und  siedet bei 155 bis<B>1,56</B>   unter 11 mm Druck.  Es mischt sich in jedem Verhältnis mit Was  ser, Alkohol, Äther, Chloroform, Benzol, ist  jedoch schwer löslich in     Petroläther.    Es soll  als Arzneimittel     verwendet    werden.

      in welcher einer der Reste     R1,        R2,        R3    eine       Carboxylgruppe,    die übrigen     Alkylreste    oder  Wasserstoff bedeuten, in umsetzungsfähige       Säureabkömmlinge,    zum Beispiel in die bis  her noch unbekannten     Säurechloride    überge-    <I>Beispiel:

  </I>    140 Teile     3,5-Dimethylisogazol-4-carbon-          säure    (Annalen der Chemie 277     [18931,     S. 174) werden mit 400 Teilen     Thionylchlo-          rid    1,5     Stunden    unter     Rückfluss    gekocht.

        Hierauf wird das überschüssige     Thionylehlo-          rid    auf dem Dampfbad     abdestilliert    und der  Rückstand im Vakuum     .destilliert.    Das     Di-          methyl-isoxazolcarbonsäurechlorid        ist        ein     farbloses 01, das bei 90   unter 12 mm siedet.  



  158 Teile     3,5-Dimethyl-isoxazol-4-carbon-          säurechlorid    werden mit 300 Teilen Äther  verdünnt und     unter    Rühren und guter Küh  lung allmählich mit 75 Teilen     Diäthylamin     versetzt.

   Die     Reaktionsmasse,    die durch Aus  scheidung von     Diäthylaminhydrochlorid    ein  breiiges Aussehen erhalten hat,     wird        nun     unter lebhaftem Rühren und     unter    Kühlung  mit 200 Teilen     9-0%iger    Natronlauge all  mählich versetzt     und    so die völlige Um  setzung des     Diäthylamins    mit dem Säure  chlorid zu Ende geführt. Zum     -Schlusse    setzt  man noch     ein    gleiches Volumen 20 %     iger    Na  tronlauge zu und trennt die     wässerige     Schicht ab.

   Nach dem     Trocknen    über festem         Kaliumhydroxyd    und     Abdestillieren    des  Äthers erhält man das     Diäthylamid    der     3,5-          Dimethylisoxazol-4-carbonsäure.    Zur Reini  gung wird im Vakuum destilliert.



  Process for the preparation of the diethylamide of 3,6-dimethylisogazole-4-carboxylic acid. Practically usable representatives of the isoxazole series have not yet been known (compare, for example, Meyer-Jacobson, Textbook of Organic Chemistry, Vol. II, third part; p. 507, last section).

   It has now been found that dialkyl-substituted amides of isoxazole carboxylic acids have valuable therapeutic properties. Compounds of the general formula are used to prepare these amides
EMI0001.0018
    leads and these are set with secondary amines.



  The subject of the present patent is a process for the preparation of the diethyl amide of 3,5-dimethylisogazole-4-carboxylic acid, which is characterized in that 3,5-dimethylisogazole-4-carboxylic acid, a condensing agent and diethylamine are allowed to act on one another .



  The new diethylamide of 3,5-dimethyl-isogazole-4-carboxylic acid melts at 24 and boils at 155 to 1.56 under 11 mm pressure. It mixes in all proportions with water, alcohol, ether, chloroform, benzene, but is sparingly soluble in petroleum ether. It is intended to be used as a medicine.

      in which one of the radicals R1, R2, R3 is a carboxyl group, the remaining alkyl radicals or hydrogen, converted into reactive acid derivatives, for example into the hitherto unknown acid chlorides. Example:

  140 parts of 3,5-dimethylisogazole-4-carboxylic acid (Annalen der Chemie 277 [18931, p. 174) are refluxed with 400 parts of thionyl chloride for 1.5 hours.

        The excess thionyl chloride is then distilled off on the steam bath and the residue is distilled in vacuo. The dimethyl isoxazole carboxylic acid chloride is a colorless oil that boils at 90 below 12 mm.



  158 parts of 3,5-dimethyl-isoxazole-4-carboxylic acid chloride are diluted with 300 parts of ether and 75 parts of diethylamine are gradually added with stirring and good cooling.

   The reaction mass, which has obtained a pulpy appearance due to the separation of diethylamine hydrochloride, is now gradually added with vigorous stirring and cooling with 200 parts of 9-0% sodium hydroxide solution and so the complete implementation of the diethylamine with the acid chloride is completed . Finally, an equal volume of 20% sodium hydroxide solution is added and the aqueous layer is separated off.

   After drying over solid potassium hydroxide and distilling off the ether, the diethylamide of 3,5-dimethylisoxazole-4-carboxylic acid is obtained. For cleaning, it is distilled in vacuo.

Claims (1)

PATENTANSPRUCH Verfahren zur Darstellung des Diäthyl- amids der 3;5-Dimethylisoxazol-4-carbon- säure, dadurch .gekennzeichnet, dass man 3,5- Dimethylisoxazol-4-carbonsäure, ein Konden- sationsmittel und Diäthylamin aufeinander einwirken lässt. Das Diäthylamid der 3, PATENT CLAIM Process for the preparation of the diethyl amide of 3; 5-dimethylisoxazole-4-carboxylic acid, characterized in that 3,5-dimethylisoxazole-4-carboxylic acid, a condensing agent and diethylamine are allowed to act on one another. The diethylamide of 3, 5-Dimethylisox- azol-4-carbonsäure schmilzt bei 24' und siedet bei 155 bis 156 unter 11 mm Druck. Es mischt sich in jedem Verhältnis mit Was ser, Alkohol, Äther, Chloroform, Benzol, ist jedoch schwer löslich in Petroläther. 5-Dimethylisoxazole-4-carboxylic acid melts at 24 'and boils at 155 to 156 under 11 mm pressure. It mixes in all proportions with water, alcohol, ether, chloroform, benzene, but is sparingly soluble in petroleum ether.
CH185280D 1935-02-22 1936-01-24 Process for the preparation of the diethylamide of 3,5-dimethylisoxazole-4-carboxylic acid. CH185280A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CH190641D CH190641A (en) 1935-02-22 1936-01-24 Process for the preparation of the piperidide of 3,5-dimethyl-isoxazole-4-carboxylic acid.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE185280X 1935-02-22

Publications (1)

Publication Number Publication Date
CH185280A true CH185280A (en) 1936-07-15

Family

ID=25721189

Family Applications (2)

Application Number Title Priority Date Filing Date
CH190641D CH190641A (en) 1935-02-22 1936-01-24 Process for the preparation of the piperidide of 3,5-dimethyl-isoxazole-4-carboxylic acid.
CH185280D CH185280A (en) 1935-02-22 1936-01-24 Process for the preparation of the diethylamide of 3,5-dimethylisoxazole-4-carboxylic acid.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CH190641D CH190641A (en) 1935-02-22 1936-01-24 Process for the preparation of the piperidide of 3,5-dimethyl-isoxazole-4-carboxylic acid.

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CH (2) CH190641A (en)

Also Published As

Publication number Publication date
CH190641A (en) 1937-04-30

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