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.Info
- 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
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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)
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)
| 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 |
-
1923
- 1923-03-14 CH CH104334D patent/CH104334A/en unknown
Cited By (2)
| 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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