CH253181A - Process for the preparation of an acylated, aliphatic aminocarboxamide. - Google Patents
Process for the preparation of an acylated, aliphatic aminocarboxamide.Info
- Publication number
- CH253181A CH253181A CH253181DA CH253181A CH 253181 A CH253181 A CH 253181A CH 253181D A CH253181D A CH 253181DA CH 253181 A CH253181 A CH 253181A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminocarboxamide
- acylated
- aliphatic
- preparation
- ethylamino
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WBGWGHYJIFOATF-UHFFFAOYSA-M potassium;methyl sulfate Chemical compound [K+].COS([O-])(=O)=O WBGWGHYJIFOATF-UHFFFAOYSA-M 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RJUIDDKTATZJFE-NSCUHMNNSA-N (e)-but-2-enoyl chloride Chemical compound C\C=C\C(Cl)=O RJUIDDKTATZJFE-NSCUHMNNSA-N 0.000 description 1
- ABRZPTWMDNJLMD-UHFFFAOYSA-N 2-(ethylamino)propanamide Chemical compound CCNC(C)C(N)=O ABRZPTWMDNJLMD-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 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
- 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 Zusatzpaten tes ist ein Verfahren zur Darstellung eines acylierien, aliphatischen Aminocarbonsäure- a.mids. Das Verfahren ist dadurch gekenn zeichnet, dass N-Crotonyl-a-äthylamino-pro- pionsäureamid am Amidstickstoff bis zum Ersatz beider Wasserstoffatome methyliert wird.
Das N-Crotonyl-a-äthylamino-propion- säuuredimethylamid der Formel
EMI0001.0016
bildet eine fast farblose Flüssigkeit vom Siedepunkt 123 bis 125 unter 0,11 mm.
Die neue Verbindung soll therapeutische Verwendung finden.
Beispiel: 23,2 Teile a-Äthylamino-propionsäureamid werden in Chloroform gelöst und bei 0 mit 10,4 Teilen Crotonsäurechlorid zur Reaktion gebracht. Vom a-Äthylamino-propionsäure- amid-ehlorhydrat wird filtriert und das Chloroform abdestilliert. Der Rückstand wird in 200 Teilen Xylol aufgenommen und mit 10 Teilen Natriumamid eine Stunde zum Sie den erhitzt. Nach dem Abkühlen werden 38 Teile Kaliummethylsulfat zugegeben und anschliessend wird im Druckgefäss auf 180 bis 190 erhitzt.
Nach beendeter Reaktion wiederholt man die Behandlung mit Natrium- amid und Kalium-methylsulfat. Dann giesst man auf Eis, sättigt die wässrige Lösung mit festem Kaliumhydroxyd und trennt die Xylollösung ab. Das Lösungsmittel wird ab destilliert und :der Rückstand im Hochvakuum rektifiziert. Die neue Verbindung zeigt den Siedepunkt 123 bis 125 unter<B>0,11</B> mm 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 method for the preparation of an acylated, aliphatic aminocarboxamide. The process is characterized in that N-crotonyl-a-ethylamino-propionic acid amide is methylated on the amide nitrogen until both hydrogen atoms are replaced.
The N-crotonyl-a-ethylamino-propionic acid dimethylamide of the formula
EMI0001.0016
forms an almost colorless liquid with a boiling point of 123 to 125 below 0.11 mm.
The new compound should find therapeutic use.
Example: 23.2 parts of a-ethylaminopropionic acid amide are dissolved in chloroform and reacted at 0 with 10.4 parts of crotonic acid chloride. The α-ethylamino-propionic acid amide ehlorhydrat is filtered off and the chloroform is distilled off. The residue is taken up in 200 parts of xylene and heated with 10 parts of sodium amide for one hour. After cooling, 38 parts of potassium methyl sulfate are added and the mixture is then heated to 180 to 190 in a pressure vessel.
After the reaction has ended, the treatment with sodium amide and potassium methyl sulfate is repeated. It is then poured onto ice, the aqueous solution is saturated with solid potassium hydroxide and the xylene solution is separated off. The solvent is distilled off and: the residue is rectified in a high vacuum. The new compound has a boiling point of 123 to 125 below <B> 0.11 </B> mm and is easily soluble in: water and organic solvents.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH253181T | 1942-12-18 | ||
| CH244952T | 1942-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH253181A true CH253181A (en) | 1948-02-15 |
Family
ID=25729007
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH253181D CH253181A (en) | 1942-12-18 | 1942-12-18 | Process for the preparation of an acylated, aliphatic aminocarboxamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH253181A (en) |
-
1942
- 1942-12-18 CH CH253181D patent/CH253181A/en unknown
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