CH99625A - Process for the preparation of diethylaminoethylcarbamic acid menthyl ester. - Google Patents

Process for the preparation of diethylaminoethylcarbamic acid menthyl ester.

Info

Publication number
CH99625A
CH99625A CH99625DA CH99625A CH 99625 A CH99625 A CH 99625A CH 99625D A CH99625D A CH 99625DA CH 99625 A CH99625 A CH 99625A
Authority
CH
Switzerland
Prior art keywords
water
diethylaminoethylcarbamic
preparation
organic solvents
menthyl ester
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH99625A publication Critical patent/CH99625A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids

Landscapes

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

Description

         

  Verfahren zur Herstellung von     Diäthylaminoäthylcarbaminsäurementhylester.       Es wurde gefunden, dass man zum     Diäthyl-          ainino.ithylcarbaminsäurenienthylester    gelan  gen kann, indem man auf Halogenameisen  säurementhylester mindestens molekulare  Mengen     as-Diäthyläthylendiamin    einwirken  lässt.  



  Die Reaktion kann sowohl in Wasser, als  auch in indifferenten organischen Lösungs  mitteln, wie zum Beispiel Äther oder Benzol  und dergleichen, beziehungsweise in Gemischen  von Wasser und organischen Lösungsmitteln  vorgenommen werden. Führt man die Reaktion  in Wasser aus, so kann man aus dem Reaktions  produkt auf Zusatz eines Alkalis, zum Beispiel  Natronlauge, die freie Base als Öl abscheiden.  



  Zweckmässig verwendet man zur Reaktion  auf 1     Mol.        Halogenameisensäureester    2     1Vfol.          as-Diäthyläthylendiamin,    um die bei der Um  setzung entstehende Salzsäure zu binden. Statt  des überschüssigen     as-Diäthyläthy        lendiamiiis     können naturgemäss auch entsprechende Men  gen von Alkalien wie zum Beispiel Natron  lauge und dergleichen verwendet     werden.     



  Der neue Körper stellt in Form der freien  Base ein in Wasser unlösliches, in den    meisten organischen Lösungsmitteln lösliches,  bei<B>0,015</B> min Druck bei 1420 siedendes Öl  dar. Das Chlorhydrat ist in Wasser und gewis  sen organischen Lösungsmitteln, wie Alkohol,  Aceton, Essigester leicht löslich.  



  Die neue Verbindung soll zu therapeu  tischen Zwecken verwendet werden.         Beispiel     Zu einer Lösung von 23,2 Teilen     as-Diä-          thyläthylendiamin    in 240 Teilen Wasser wer  den unter Rühren und Eiskühlung 20,8 Teile       Chlorameisensäurementhylester,    gelöst in 50  Teilen Äther,     zugetropft.    Nach vollendeter  Umsetzung wird Natronlauge zugesetzt, der  Äther abgehoben und getrocknet. Der Äther  rückstand ist fast reiner     Diäthylaminoäthyl-          carbaminsäurementhylester.    Derselbe wird  durch Destillation im Hochvakuum gereinigt.



  Process for the preparation of diethylaminoethylcarbamic acid menthyl ester. It has been found that ethyl diethyl ainino.ithylcarbamic acid can be obtained by letting at least molecular amounts of as-diethylethylenediamine act on the tungsten acid halide.



  The reaction can be carried out both in water and in inert organic solvents, such as ether or benzene and the like, or in mixtures of water and organic solvents. If the reaction is carried out in water, the free base can be separated out as an oil from the reaction product by adding an alkali, for example sodium hydroxide solution.



  It is expedient to use 2 1Vfol for the reaction to 1 mole of haloformic acid ester. as-diethylethylenediamine, in order to bind the hydrochloric acid formed during the implementation. Instead of the excess a-diethylethylenediamine, corresponding quantities of alkalis, such as sodium hydroxide and the like, can naturally also be used.



  In the form of the free base, the new body is an oil that is insoluble in water, soluble in most organic solvents and boiling at 1420 at <B> 0.015 </B> min pressure. The hydrochloride is in water and certain organic solvents, such as Easily soluble in alcohol, acetone and ethyl acetate.



  The new compound is intended to be used for therapeutic purposes. EXAMPLE To a solution of 23.2 parts of as-diethylethylenediamine in 240 parts of water, 20.8 parts of menthyl chloroformate, dissolved in 50 parts of ether, are added dropwise with stirring and ice-cooling. After the reaction is complete, sodium hydroxide solution is added, the ether is lifted off and dried. The ether residue is almost pure diethylaminoethyl carbamic acid menthyl ester. The same is purified by distillation in a high vacuum.

Claims (1)

PATENTANSPRUCH: Zierfahren zur Herstellung von Diä- thylaminoäthylcaruaminsäurementhylestei-, da durch gekennzeichnet, dass man auf Halogen- ameisensäurementhylester mindestens moleku- lareMengen as-Diäthyläthylendiamin einwirken lässt. Der neue Körper stellt in Form der freien Base ein in Wasser unlösliches, in den meisten organischen Lösungsmitteln lösliches, bei 0,015 mm Druck bei 142 siedendes<B>01</B> dar. Das Chlorhydrat ist in Wasser und gewis- sen organischen Lösungsmitteln, wie Alkohol, Aceton, Essigester leicht löslich. PATENT CLAIM: Ornamental process for the production of diethylaminoethylcaruamic acid, characterized in that at least molecular amounts of as-diethylethylenediamine are allowed to act on the manganese acid halide. In the form of the free base, the new body represents a <B> 01 </B> which is insoluble in water, soluble in most organic solvents and boiling at 0.015 mm pressure at 142. The chlorohydrate is in water and certain organic solvents, Easily soluble such as alcohol, acetone, ethyl acetate. Die neue Verbindung soll zu therapeu tischen Zwecken verwendet werden. The new compound is intended to be used for therapeutic purposes.
CH99625D 1922-02-10 1922-02-10 Process for the preparation of diethylaminoethylcarbamic acid menthyl ester. CH99625A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH99625T 1922-02-10

Publications (1)

Publication Number Publication Date
CH99625A true CH99625A (en) 1923-06-01

Family

ID=4357599

Family Applications (1)

Application Number Title Priority Date Filing Date
CH99625D CH99625A (en) 1922-02-10 1922-02-10 Process for the preparation of diethylaminoethylcarbamic acid menthyl ester.

Country Status (1)

Country Link
CH (1) CH99625A (en)

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