CH253182A - Process for the preparation of an acylated, aliphatic aminocarboxamide. - Google Patents
Process for the preparation of an acylated, aliphatic aminocarboxamide.Info
- Publication number
- CH253182A CH253182A CH253182DA CH253182A CH 253182 A CH253182 A CH 253182A CH 253182D A CH253182D A CH 253182DA CH 253182 A CH253182 A CH 253182A
- Authority
- CH
- Switzerland
- Prior art keywords
- acylated
- preparation
- aliphatic
- aminocarboxamide
- propylamino
- 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
- 238000009835 boiling Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 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
- RJUIDDKTATZJFE-NSCUHMNNSA-N (e)-but-2-enoyl chloride Chemical compound C\C=C\C(Cl)=O RJUIDDKTATZJFE-NSCUHMNNSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WBGWGHYJIFOATF-UHFFFAOYSA-M potassium;methyl sulfate Chemical compound [K+].COS([O-])(=O)=O WBGWGHYJIFOATF-UHFFFAOYSA-M 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 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
- 238000002560 therapeutic procedure Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung eines acylierten, aliphatischen Aminocarbonsäureamids Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Darstellung eines acylierten, aliphatischen Aminocarbonsäure- amids. Das Verfahren ist dadurch gekenn- s zeichnet, dass N-Crotonyl-a-(n-propylamino)- n-buttersäurea,mid am Amidstickstoff bis zum Ersatz beider Wasserstoffatome methyliert wird.
Das N-Crotonyl-a-(n-propylamino)-n-but- tersäuredimethylamid der Formel
EMI0001.0017
bildet eine fast farblose Flüssigkeit vom Siedepunkt 128 bis 130 unter 0,25 mm.
Die neue Verbindung soll therapeutische \'erwendung finden. Beispiel: 26 Teile a-(n-Propylamino)-n-buttersäure- a.mid werden in Chloroform gelöst und bei 0 mit 10,4 Teilen Crotonsäurechlorid zur Re aktion gebracht. Vom a-(n-Propylamino)-n- buttersäureamid-chlorhydrat wird filtriert und das Chloroform abdestilliert. Der Rück stand wird in 200 Teilen Xylol aufgenommen and mit 10 Teilen Na.triumamid eine Stunde zum Sieden erhitzt.
Nach dem Abkühlen wer- deri 38 Teile IZalium-methylsulfat zugegeben und anschliessend wird im Druckgefäss auf <B>180</B> bis 190 erhitzt. Nach beendeter Reak tion wiederholt man die Behandlung mit Na- triumamid und ga,lium-methylsulfat. Dann giesst man auf Eis, sättigt die wässrige Lösung mit festem Kaliumhydroxyd und trennt die Yylollösung ab. Das Lösungsmittel wird ab destilliert und der Rückstand im Hochvakuum rektifiziert.
Die neue Verbindung zeigt den Siedepunkt 128 bis 130 unter 0,25 mm und ist leicht löslich in Wasser und organischen Lösungsmitteln.
Process for the preparation of an acylated, aliphatic aminocarboxylic acid amide 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 N-crotonyl-a- (n-propylamino) -n-butyric acid amide is methylated on the amide nitrogen until both hydrogen atoms are replaced.
The N-crotonyl-a- (n-propylamino) -n-but-tersäuredimethylamid of the formula
EMI0001.0017
forms an almost colorless liquid with a boiling point of 128 to 130 below 0.25 mm.
The new compound is intended to be used in therapy. Example: 26 parts of a- (n-propylamino) -n-butyric acid a.mid are dissolved in chloroform and reacted at 0 with 10.4 parts of crotonic acid chloride. The a- (n-propylamino) -n-butyric acid amide chlorohydrate is filtered off and the chloroform is distilled off. The residue is taken up in 200 parts of xylene and heated to boiling with 10 parts of sodium triumamide for one hour.
After cooling, 38 parts of potassium methyl sulfate are added and the mixture is then heated to between 180 and 190 in a pressure vessel. When the reaction has ended, the treatment with sodium amide and galum methyl sulfate is repeated. Then it is poured onto ice, the aqueous solution is saturated with solid potassium hydroxide and the yylene 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 128 to 130 below 0.25 mm and is easily soluble in water and organic solvents.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH244952T | 1942-12-18 | ||
| CH253182T | 1942-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH253182A true CH253182A (en) | 1948-02-15 |
Family
ID=25729008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH253182D CH253182A (en) | 1942-12-18 | 1942-12-18 | Process for the preparation of an acylated, aliphatic aminocarboxamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH253182A (en) |
-
1942
- 1942-12-18 CH CH253182D patent/CH253182A/en unknown
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