CH185061A - Process for the preparation of a substituted amide of a fatty aromatic acid. - Google Patents
Process for the preparation of a substituted amide of a fatty aromatic acid.Info
- Publication number
- CH185061A CH185061A CH185061DA CH185061A CH 185061 A CH185061 A CH 185061A CH 185061D A CH185061D A CH 185061DA CH 185061 A CH185061 A CH 185061A
- Authority
- CH
- Switzerland
- Prior art keywords
- diphenylacetic acid
- preparation
- starting material
- substituted amide
- diphenylacetic
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines substituierten Amides einer fettaromatischen Säure. Es wurde gefunden, dass man zu einem substituierten Amid einer fettaromatischen Säure gelangen kann, wenn man eine Ver bindung, die das Radial der Formel
EMI0001.0004
enthält, wie zum Beispiel Diphenylessig- säure, ihr Anhydrid, ihre Ester oder Halo genide, zuerst mit Aminoäthanol reagieren lässt,
in dem erhaltenen Diphenylessigsäure- 2-ogyäthylamid die Ogygruppe durch eine Halogengruppe ersetzt und auf das Halogen derivat Diäthylamin einwirken lässt.
Das so erhaltene Diphenylessigsäure-2- diäthylaminoäthylamid ist identisch mit der in der Patentschrift Nr.182892 beschriebe nen Verbindung.
Die neue Verbindung soll therapeutische Verwendung finden.
<I>Beispiel:</I> 42 Teile Diphenylessigsäure und 12 Teile Aminoäthanol werden während zwei Stunden auf 200' erhitzt, wobei man das bei der Kondensation sich bildende Wasser abdestil- lieren lädt.
Nach beendeter Umsetzung wird das entstandene Diphenylessigsäure-2-ogy- äthylamid mit Petroläther veirieben, worauf es alsbald erstarrt. Durch Umkristallisieren aus Benzol gewinnt man es in weissen Kri stallnadeln vom F. 119 bis 121 . An Stelle von Diphenylessigsäure kann man auch einen Diphenylessigsäureester verwenden.
1ä Teile Diphenylessigsäure-2-ogyäthyl- amid werden in 100 Teilen Chloroform ge löst und mit 10,.5 Teilen Phosphorpenta- chlorid zwei Stunden auf<B>60'</B> erwärmt. Die Reaktionsmasse wird in Äther aufgenom men, die ätherische Lösung mit Soda und Wasser ,gewaschen und dann über Kalium karbonat getrocknet.
Nach Verdampfen des Lösungsmittels erhält man das Diphenyl- essigsäure-2-chloräthylamid, das aus Ilega- hydrotoluol umkristallisiert farblose Kri stalle vom F. 125 bildet. In analoger Weise kann das Bromderivat hergestellt werden. 27,5 Teile Diphenylessigsäure - 2 - chlor äthylamid werden mit 18 Teilen Diäthyl- amin im Bombenrohr während zirka 8 Stun den auf 120' erhitzt.
Nun nimmt man in verdünnter Salzsäure auf, fällt aus der wässrigen Lösung das Diphenylessigsäure-2- diäthylaminoäthylamid mit Soda aus und reinigt es durch Umkristallisieren.
Process for the preparation of a substituted amide of a fatty aromatic acid. It has been found that a substituted amide of a fatty aromatic acid can be obtained by using a compound which has the radial of the formula
EMI0001.0004
contains, such as diphenylacetic acid, its anhydride, its esters or halides, first reacts with aminoethanol,
in the obtained diphenylacetic acid 2-ogyäthylamid the Ogygruppe replaced by a halogen group and the halogen derivative diethylamine can act.
The diphenylacetic acid-2-diethylaminoethylamide obtained in this way is identical to the compound described in Patent No. 182892.
The new compound should find therapeutic use.
<I> Example: </I> 42 parts of diphenylacetic acid and 12 parts of aminoethanol are heated to 200 ° for two hours, during which the water that forms during the condensation is charged to distil off.
When the reaction is complete, the 2-ogyethyl-diphenylacetic acid formed is rubbed with petroleum ether, whereupon it soon solidifies. By recrystallizing from benzene, it is obtained in white crystal needles with a F. 119 to 121. Instead of diphenylacetic acid, a diphenylacetic acid ester can also be used.
1ä parts of diphenylacetic acid-2-ogyäthyl- amid are dissolved in 100 parts of chloroform and heated with 10.5 parts of phosphorus pentachloride to <B> 60 '</B> for two hours. The reaction mass is taken up in ether, the ethereal solution washed with soda and water and then dried over potassium carbonate.
After evaporation of the solvent, diphenylacetic acid-2-chloroethylamide is obtained, which, when recrystallized from legahydrotoluene, forms colorless crystals with a melting point of 125. The bromine derivative can be prepared in an analogous manner. 27.5 parts of diphenylacetic acid - 2 - chloroethylamide are heated to 120 'with 18 parts of diethylamine in a sealed tube for about 8 hours.
Now it is taken up in dilute hydrochloric acid, the diphenylacetic acid-2-diethylaminoethylamide is precipitated from the aqueous solution with soda and it is purified by recrystallization.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH185061T | 1934-09-18 | ||
| CH175470T | 1934-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH185061A true CH185061A (en) | 1936-06-30 |
Family
ID=25719706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH185061D CH185061A (en) | 1934-09-18 | 1934-09-18 | Process for the preparation of a substituted amide of a fatty aromatic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH185061A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0383256A2 (en) * | 1989-02-14 | 1990-08-22 | Fujisawa Pharmaceutical Co., Ltd. | A novel substituted-acetamide compound and a process for the preparation thereof |
| US5192779A (en) * | 1989-02-14 | 1993-03-09 | Fujisawa Pharmaceutical Co., Ltd. | Substituted-acetamide compound and a process for the preparation thereof |
-
1934
- 1934-09-18 CH CH185061D patent/CH185061A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0383256A2 (en) * | 1989-02-14 | 1990-08-22 | Fujisawa Pharmaceutical Co., Ltd. | A novel substituted-acetamide compound and a process for the preparation thereof |
| EP0383256A3 (en) * | 1989-02-14 | 1992-01-02 | Fujisawa Pharmaceutical Co., Ltd. | A novel substituted-acetamide compound and a process for the preparation thereof |
| US5192779A (en) * | 1989-02-14 | 1993-03-09 | Fujisawa Pharmaceutical Co., Ltd. | Substituted-acetamide compound and a process for the preparation thereof |
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