CH240399A - Process for the preparation of an acylated, aliphatic aminocarboxamide. - Google Patents
Process for the preparation of an acylated, aliphatic aminocarboxamide.Info
- Publication number
- CH240399A CH240399A CH240399DA CH240399A CH 240399 A CH240399 A CH 240399A CH 240399D A CH240399D A CH 240399DA CH 240399 A CH240399 A CH 240399A
- Authority
- CH
- Switzerland
- Prior art keywords
- acylated
- preparation
- aliphatic
- aminocarboxamide
- acid dimethylamide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims description 4
- 125000001931 aliphatic group Chemical group 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 2
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines acylierten, aliphatischen Aminocarbonsäureamids. Gegenstand des vorliegenden Zusatz patentes ist ein Verfahren zur Darstellung eines acylierten, aliphatischen Aminocarbon- säureamids. Das Verfahren ist dadurch ge kennzeichnet, dass ein a-Halogen-pro#pionsäure- dimethylamid mit Isopropylamin umgesetzt und das Reaktionsprodukt mit einer das Ra dikal der Crotonsäure abgebenden Verbin dung acyliert wird.
Das N-Crotonyl-a-(isopropylamino)-pro- pionsäuredimethylamid der Formel
EMI0001.0015
bildet farblose Kristalle vom Schmelzpunkt 82-85 .
Die neue Verbindung soll therapeutische Verwendung finden. <I>Beispiel:</I> 31,6 Teile a-(Isopropylamino)-propion- säuredimethylamid, $p" 90-92 (darge stellt aus a-Brom-propionsäuredimethylamid durch Erhitzen mit Isopropylamin), werden in 200 Teilen Äther gelöst und unter Rühren und Kühlen 10,4 Teile Cro-tonsäurechlorid zugetropft. Nach 2stündigem Rühren wird vom a - (Isopropylamino)
- propionsäuredi - methylamid-chlorhydrat abfiltriert und die ätherische Lösung mit gesättigter Kalilauge geschüttelt. Nach dem Abdestillieren des Lö sungsmittels wird das Reaktionsprodukt im Hochvakuum rektifiziert. Die neue Verbin dung siedet bei 121-122 unter 0,1 mm, schmilzt bei 82-85 und ist leicht löslich in Wasser und organischen Lösungsmitteln.
Process for the preparation of an acylated, aliphatic aminocarboxamide. The subject of the present additional patent is a process for the preparation of an acylated, aliphatic aminocarboxylic acid amide. The process is characterized in that an α-halo-propionic acid dimethylamide is reacted with isopropylamine and the reaction product is acylated with a compound which releases the radical of crotonic acid.
The N-crotonyl-a- (isopropylamino) -propionic acid dimethylamide of the formula
EMI0001.0015
forms colorless crystals with a melting point of 82-85.
The new compound should find therapeutic use. <I> Example: </I> 31.6 parts of a- (isopropylamino) -propionic acid dimethylamide, $ p "90-92 (shown from a-bromopropionic acid dimethylamide by heating with isopropylamine), are dissolved in 200 parts of ether and 10.4 parts of cotonic acid chloride are added dropwise with stirring and cooling.
- Propionic acid dimethylamide chlorohydrate filtered off and the ethereal solution shaken with saturated potassium hydroxide solution. After the solvent has been distilled off, the reaction product is rectified in a high vacuum. The new compound boils below 0.1 mm at 121-122, melts at 82-85 and is easily soluble in water and organic solvents.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH234453T | 1942-12-18 | ||
| CH240399T | 1942-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH240399A true CH240399A (en) | 1945-12-15 |
Family
ID=25727916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH240399D CH240399A (en) | 1942-12-18 | 1942-12-18 | Process for the preparation of an acylated, aliphatic aminocarboxamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH240399A (en) |
-
1942
- 1942-12-18 CH CH240399D patent/CH240399A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH240399A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240379A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH149007A (en) | Process for the preparation of a halogen-containing basic ether. | |
| CH240389A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240376A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240380A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240373A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH243014A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240375A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240378A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240374A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240391A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240396A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240385A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240381A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240377A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240393A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240394A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240386A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240372A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240382A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240398A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240388A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240387A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240371A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. |