CH253183A - Process for the preparation of an acylated, aliphatic aminocarboxamide. - Google Patents
Process for the preparation of an acylated, aliphatic aminocarboxamide.Info
- Publication number
- CH253183A CH253183A CH253183DA CH253183A CH 253183 A CH253183 A CH 253183A CH 253183D A CH253183D A CH 253183DA CH 253183 A CH253183 A CH 253183A
- 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
- 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
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- BDRTVPCFKSUHCJ-UHFFFAOYSA-N molecular hydrogen;potassium Chemical compound [K].[H][H] BDRTVPCFKSUHCJ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 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. Cregenstaiid des vorliegenden Zusatzpaten tes ist ein Verfahren.
zur Darstellung eines acylierten, a_liphatischen Aminocarbonsäure- amids. Das Verfahren ist dadurch gekenn zeichnet, dass N-Propionyl-a-(n-propylamino)- n-buttersä.ureamid am Amidstickstoff bis zum Ersatz beider Wasserstoffatome methyliert wird.
Das N-Propionyl-a-(n-propylamino)-n-but- tersäiiredimethylamid der Formel
EMI0001.0017
bildet eine farblose Flüssigkeit vom Siede punkt 119 bis 120 unter 0,2 mm.
Die neue Verbindung soll therapeutische Verwendung finden.
Beispiel: 28,8 Teile a-(n-Propylamino)-n-butter- säureamid werden in Chloroform gelöst und bei 0 mit 9,4 Teilen Propionylchlorid zur Reaktion gebracht. Von a-(n-Propylamino)- n-buttersäureamid-chlorhydrat wird filtriert und das Chloroform abdestilliert. Der Rück stand wird in 200 Teilen Xylol aufgenom men und mit 10 Teilen Natriumamid eine Stunde zum Sieden erhitzt.
Nach dem Ab kühlen werden. <B>38</B> Teile Kalium-methylsulfat zugegeben, und anschliessend wird im Druck gefäss auf 180 bis 190 erhitzt. Nach be endeter Reaktion wiederholt man die Behand lung mit Natriumamid und Kalium-methyl- sulfat. Dann giesst man auf Eis, sättigt die wässrige Lösung mit festem Kaliumhydrogyd und trennt die Xylollösung ab.
Das Lösungs mittel wird abdestilliert und der Rückstand im Hochvakuum rektifiziert. Die neue Ver bindung zeigt den Siedepunkt 119 bis 120 unter 0,2 mm und ist leicht löslich in Wasser und organischen Lösungsmitteln.
Process for the preparation of an acylated, aliphatic aminocarboxamide. Cregenstaiid 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-propionyl-a- (n-propylamino) - n-butyric acid amide is methylated on the amide nitrogen until both hydrogen atoms are replaced.
The N-propionyl-a- (n-propylamino) -n-buttersäiiredimethylamid of the formula
EMI0001.0017
forms a colorless liquid with a boiling point of 119 to 120 below 0.2 mm.
The new compound should find therapeutic use.
Example: 28.8 parts of a- (n-propylamino) -n-butyric acid amide are dissolved in chloroform and reacted at 0 with 9.4 parts of propionyl chloride. 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 amide for one hour.
Be cool after cooling. 38 parts of potassium methyl sulfate are added, and the mixture is then heated to 180 to 190 in a pressure vessel. When 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 hydrogen 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 119 to 120 below 0.2 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 | ||
| CH253183T | 1942-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH253183A true CH253183A (en) | 1948-02-15 |
Family
ID=25729009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH253183D CH253183A (en) | 1942-12-18 | 1942-12-18 | Process for the preparation of an acylated, aliphatic aminocarboxamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH253183A (en) |
-
1942
- 1942-12-18 CH CH253183D patent/CH253183A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH253184A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH253180A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH253182A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH253181A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240379A (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. | |
| CH245887A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH235516A (en) | Process for the preparation of , -dimethyl-succinic acid-bis-diethylamide. | |
| CH245885A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240396A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240397A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH245884A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240372A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240386A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240383A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240381A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH245883A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH268086A (en) | Process for the preparation of an acylated aliphatic aminocarboxamide. | |
| CH310171A (en) | Process for the preparation of a pharmaceutically active compound. | |
| CH245886A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240398A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH240377A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. | |
| CH221827A (en) | Process for the production of a new condensation product. | |
| CH240385A (en) | Process for the preparation of an acylated, aliphatic aminocarboxamide. |