CH100408A - Process for the preparation of diethylaminoethyliminodicarboxylic acid phenylethyl ester. - Google Patents
Process for the preparation of diethylaminoethyliminodicarboxylic acid phenylethyl ester.Info
- Publication number
- CH100408A CH100408A CH100408DA CH100408A CH 100408 A CH100408 A CH 100408A CH 100408D A CH100408D A CH 100408DA CH 100408 A CH100408 A CH 100408A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- diethylaminoethyliminodicarboxylic
- water
- phenylethyl ester
- acid phenylethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- FVBKKAFQPWIKQE-UHFFFAOYSA-N CCN(CC)CCN(C(O)=O)C(OCCC1=CC=CC=C1)=O Chemical compound CCN(CC)CCN(C(O)=O)C(OCCC1=CC=CC=C1)=O FVBKKAFQPWIKQE-UHFFFAOYSA-N 0.000 title claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DKULSTMKCYRQCP-UHFFFAOYSA-N 2-phenylethyl carbonochloridate Chemical compound ClC(=O)OCCC1=CC=CC=C1 DKULSTMKCYRQCP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- -1 phenylethyl ester Chemical class 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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 Diäthylaminoäthyliminodiearbonsäurephenyläthylester. Es wurde gefunden, dass man zum Diäthylaminoäthyliminodicarbonsäur ep henyl - äthylester gelangen kann, indem man auf 2 Mo1. Halogenameisensäurephenyläthylester 1 Mol. as-Diäthylendiamin in Gegenwart von Alkali einwirken lässt.
Die Reaktion kann sowohl in Wasser, als auch in indifferenten organischen Lösungs- tnitteln, wie z. B. Äther oder Benzol und dergleichen bezw. in Gemischeid von Wasser und organischen Lösungsmitteln vorgenom men werden. Führt man die Reaktion in Wasser aus, so kann man aus dem Reaktions produkt durch einen Überschuss eines Alkalis, z. B. Natronlauge, die freie Base als 01 ab scheiden.
Der neue Körper stellt in Form der freien Base ein in Wasser unlösliches, in den mei sten organischen Lösungsmitteln lösliches, unter 0,05 mm Druck bei 200-202 o sie dendes 01 dar. Das Chlorhydrat ist in Wasser, Alkohol und Aceton leicht löslich.
Die neue Verbindung soll zu therapeu tischen Zwecken verwendet werden. <I>Beispiel:</I> <B>116</B> Teile as-Diäthyläthylendiamin wer den in 400 Teilen Eis und 100 Teilen Wasser gelöst und hierzu unter Rühren 370 Teile Chlor- ameisensäurephenyläthylester unter gleioh- zeitigem Zutropfen von 400 Teilen 10 o/oiger Natronlauge zugefügt. Hierauf wird das Re aktionsgemisch mit Alkali übersättigt, die Base in Äther aufgenommen und über Pott asche getrocknet. Der Ätherrückstand wird im Vakuum destilliert.
Process for the preparation of diethylaminoethyliminodiearboxylic acid phenylethyl ester. It has been found that you can get to diethylaminoäthyliminodicarbonsäurep henyl - ethyl ester by increasing to 2 Mo1. Phenylethyl haloformate 1 mol. As-diethylenediamine can act in the presence of alkali.
The reaction can be carried out both in water and in inert organic solvents, such as B. ether or benzene and the like BEZW. in a mixture of water and organic solvents. If you carry out the reaction in water, you can from the reaction product by an excess of an alkali, for. B. sodium hydroxide solution, the free base as 01 separate from.
In the form of the free base, the new body is insoluble in water, soluble in most organic solvents, under 0.05 mm pressure at 200-202 o sie dendes 01. The hydrochloride is easily soluble in water, alcohol and acetone.
The new compound is intended to be used for therapeutic purposes. <I> Example: </I> <B> 116 </B> parts of as-diethylethylenediamine are dissolved in 400 parts of ice and 100 parts of water and, with stirring, 370 parts of phenylethyl chloroformate with simultaneous dropwise addition of 400 parts of 10 o / o sodium hydroxide solution added. The reaction mixture is then supersaturated with alkali, the base is taken up in ether and dried over pot ash. The ether residue is distilled in vacuo.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH100408T | 1922-02-10 | ||
| CH99625T | 1922-02-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH100408A true CH100408A (en) | 1923-08-01 |
Family
ID=25705623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH100408D CH100408A (en) | 1922-02-10 | 1922-02-10 | Process for the preparation of diethylaminoethyliminodicarboxylic acid phenylethyl ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH100408A (en) |
-
1922
- 1922-02-10 CH CH100408D patent/CH100408A/en unknown
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