CH104334A - Process for the preparation of a-ethyl-a-diethylaminomethylacetacetic acid ethyl ester. - Google Patents

Process for the preparation of a-ethyl-a-diethylaminomethylacetacetic acid ethyl ester.

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Publication number
CH104334A
CH104334A CH104334DA CH104334A CH 104334 A CH104334 A CH 104334A CH 104334D A CH104334D A CH 104334DA CH 104334 A CH104334 A CH 104334A
Authority
CH
Switzerland
Prior art keywords
ethyl
acetic acid
diethylaminomethylacetacetic
ethyl ester
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 CH104334A publication Critical patent/CH104334A/en

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Description

  

  Verfahren zur Darstellung von     a-Äthyl-a-diäthylaminomethylacetessigsäureäthylester.       Es wurde gefunden, dass man durch Kon  densation von     a-Äthylacetessigsäureäthylester     mit Formaldehyd und     Diäthylamin    zum     a-          Äthyl-        a-diäthylaminomethyl    -     acetessigsäure-          äthylester    gelangt.  



  Das     Diäthylamin    kann als freie Base  oder in Form seiner Polymeren zur Anwen  dung kommen. Die Reaktion lässt sich ge  gebenenfalls in Gegenwart von Kondensations  mitteln durchführen. Anstatt alle drei Be-         standteile    zugleich in Reaktion zu bringen,  können auch ohne Beeinflussung des Reak  tionsverlaufes vorerst je zwei von ihnen kon  densiert und hierauf mit dem dritten in Re  aktion gebracht werden. So lassen sich zum  Beispiel Formaldehyd und     Diäthylamin    ohne  weiteres durch ihr Kondensationsprodukt, das       Diäthylaminomethylol    ersetzen.  



  Die Reaktion erfolgt nach folgendem  Schema  
EMI0001.0013     
    Der     a-Äthyl-a-diäthyhlaminomethyl-acet-          essigsäureäthylester    bildet ein farbloses 01  vom Siedepunkt 123 o bei 8 mm Druck. In  Wasser ist er schwer, in organischen Lösungs  mitteln wie auch in Mineralsäuren ist er leicht  löslich. Der Ester soll als solcher oder als  Zwischenprodukt     füi    pharmazeutische Zwecke       Verwendung    finden.

           Beispiel:     Zu 146 Teilen wässerigem 50     %igem        Di-          äthylamin    gibt man unter Kühlung 86 Teile  wässerige     Formaldehydlösung    von     35    0% und  hierauf in einer Portion 158 Teile     Äthylacet-          essigsäureäthylester.    Man verrührt kurze Zeit  und neutralisiert dann unter Kühlung mit  Mineralsäure. Neutrale Körper lassen sich      durch     Ausäthern    entfernen. Auf Zusatz von       lialiumkarbonat    fällt die neue Base als<B>01</B>  aus.

   Durch     Ausäthern,    Trocknen und Ver  dunsten des Äthers gewinnt man den     "j.-Äthyl-          cc-diäthylaminomethyl-acetessigsäureäthylester     in sehr guter Ausbeute. Durch Destillation  im Vakuum lässt er sich     reinigen.  



  Process for the preparation of a-ethyl-a-diethylaminomethylacetacetic acid ethyl ester. It has been found that condensation of a-ethyl acetic acid ethyl ester with formaldehyde and diethylamine leads to a-ethyl-a-diethylaminomethyl-acetic acid ethyl ester.



  The diethylamine can be used as a free base or in the form of its polymers. The reaction can optionally be carried out in the presence of condensation agents. Instead of reacting all three components at the same time, without influencing the course of the reaction, two of them can be condensed for the time being and then brought into reaction with the third. For example, formaldehyde and diethylamine can easily be replaced by their condensation product, diethylaminomethylol.



  The reaction takes place according to the following scheme
EMI0001.0013
    The a-ethyl-a-diethyhlaminomethyl-acet-acetic acid ethyl ester forms a colorless oil with a boiling point of 123 ° at 8 mm pressure. It is difficult in water, and it is easily soluble in organic solvents and mineral acids. The ester is intended to be used as such or as an intermediate for pharmaceutical purposes.

           Example: 86 parts of 35% aqueous formaldehyde solution are added to 146 parts of aqueous 50% diethylamine with cooling, followed by 158 parts of ethyl acetate in one portion. The mixture is stirred for a short time and then neutralized with mineral acid while cooling. Neutral bodies can be removed by etherification. Upon addition of lialium carbonate, the new base precipitates as <B> 01 </B>.

   Ethyl-cc-diethylaminomethyl-acetic acid ethyl ester is obtained in a very good yield by etherifying, drying and evaporating the ether. It can be purified by distillation in vacuo.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung des a-Ätliy l-cc- diäthy laminomethyl-acetessigsäurei2ithylesters, dadurch gekennzeichnet, dass a-Äthylacetessig- säure < ithy fester mit Formaldehyd und Diäthyl- amin kondensiert wird. Der --Äthyl. -a-diäthylamiiiomethyl-acet- essigsäureäthy fester bildet ein farbloses 0I vom Siedepunkt 123<B>'</B> ' bei 8 mm Druck. PATENT CLAIM: Process for the production of the a-ethyl-cc-diethyl laminomethyl-acetic acid ethyl ester, characterized in that a-ethyl-acetic acid <ithy is condensed with formaldehyde and diethylamine. The --ethyl. -a-diethylamiiiomethyl-acet- acetic acid ethy solid forms a colorless oil with a boiling point of 123 <B> '</B>' at 8 mm pressure. In Wasser ist er schwer, in organischen Lösungs mitteln wie auch in Mineralsäuren ist er leicht löslich. Der Ester soll als solcher oder als Zwischenprodukt für pharmazeutische Zwecke Verwendung finden. It is difficult in water, and it is easily soluble in organic solvents and mineral acids. The ester is intended to be used as such or as an intermediate for pharmaceutical purposes.
CH104334D 1923-03-14 1923-03-14 Process for the preparation of a-ethyl-a-diethylaminomethylacetacetic acid ethyl ester. CH104334A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH104334T 1923-03-14

Publications (1)

Publication Number Publication Date
CH104334A true CH104334A (en) 1924-05-01

Family

ID=4363174

Family Applications (1)

Application Number Title Priority Date Filing Date
CH104334D CH104334A (en) 1923-03-14 1923-03-14 Process for the preparation of a-ethyl-a-diethylaminomethylacetacetic acid ethyl ester.

Country Status (1)

Country Link
CH (1) CH104334A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2480683A (en) * 1946-10-29 1949-08-30 Merck & Co Inc Reduction of compounds containing an active methylene group
US2752352A (en) * 1952-12-20 1956-06-26 Heyden Pharmacal Company Derivatives of the esters of beta-ketonic acids and process

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2480683A (en) * 1946-10-29 1949-08-30 Merck & Co Inc Reduction of compounds containing an active methylene group
US2752352A (en) * 1952-12-20 1956-06-26 Heyden Pharmacal Company Derivatives of the esters of beta-ketonic acids and process

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