CH253176A - Process for the preparation of an acylated, aliphatic aminocarboxamide. - Google Patents
Process for the preparation of an acylated, aliphatic aminocarboxamide.Info
- Publication number
- CH253176A CH253176A CH253176DA CH253176A CH 253176 A CH253176 A CH 253176A CH 253176D A CH253176D A CH 253176DA CH 253176 A CH253176 A CH 253176A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminocarboxamide
- aliphatic
- preparation
- acylated
- parts
- 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
- 239000007788 liquid Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000003756 stirring Methods 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 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 Aminocarbonsäureami@s- Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Darstellung eines ae-ylierten, aliphatischen Aminocarbonsäure- amids. Das Verfahren ist dadurch gekenn zeichnet, dass N-Crotonyl-a-amino-propion- säuredimethylamid äthyliert wird.
Daz N- Crotünyl - a - äthylamino-propion- säuredimethylamid der Formel
EMI0001.0014
bildet eine fast farblose Flüssigkeit vom Siedepunkt 123 bis 125 unter 0,11 mm. Die neue Verbindung soll therapeutische Verwen dung finden.
<I>Beispiel:</I> 23,2 Teile a-Amino-propionsäuredimethyl- amid werden in 200 Teilen Äther gelöst und unter Rühren und Kühlen 10,4 Teile Croton- säureehlorid zugetropft. Nach 2stündigem Rühren wird vom a-Amino-propionsäuredime- thylamid-ehlorhydrat filtriert, vom Äther durch Destillation befreit und das Produkt fraktio niert; Siedepunkt 165 bis 168 unter 0,3 mm.
18,4 Teile des erhaltenen N-Crotonyl-a-amino- propionsäurz"dimethylamids in 200 Teilen Zylol werden mit 4 Teilen Natriumamid einige Zeit zum Sieden erhitzt. Nach dem Abkühlen wird mit 32 Teilen Äthyljodid ver setzt und im Druckgefäss auf 150 bis 160 erhitzt. Das Reaktionsprodukt wird mit ge sättigter Kalilauge durchgeschüttelt und die Xylollösung abgetrennt. Nach dem Abdestil- lieren des Xylols wird der Rückstand im Hochvakuum rektifiziert.
Die neue Verbin dung zeigt den Siedepunkt 128 bis 125 unter 0,11 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 ae-ylated, aliphatic aminocarboxamide. The process is characterized in that N-crotonyl-a-amino-propionic acid dimethylamide is ethylated.
Daz N-Crotünyl-a-ethylamino-propionic acid dimethylamide of the formula
EMI0001.0014
forms an almost colorless liquid with a boiling point of 123 to 125 below 0.11 mm. The new compound is intended to find therapeutic use.
<I> Example: </I> 23.2 parts of a-amino propionic acid dimethyl amide are dissolved in 200 parts of ether and 10.4 parts of crotonic acid chloride are added dropwise with stirring and cooling. After stirring for 2 hours, the a-amino propionic acid dimethylamide is filtered off, freed from ether by distillation and the product is fractionated; Boiling point 165 to 168 below 0.3 mm.
18.4 parts of the resulting N-crotonyl-a-aminopropionic acid dimethylamide in 200 parts of cylol are heated to the boil with 4 parts of sodium amide for some time. After cooling, 32 parts of ethyl iodide are added and the mixture is heated to 150 to 160 parts in a pressure vessel The reaction product is shaken through with saturated potassium hydroxide solution and the xylene solution is separated off. After the xylene has been distilled off, the residue is rectified in a high vacuum.
The new compound has a boiling point of 128 to 125 below 0.11 mm and is easily soluble in water and organic solvents.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH253176T | 1942-12-18 | ||
| CH244952T | 1942-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH253176A true CH253176A (en) | 1948-02-15 |
Family
ID=25729002
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH253176D CH253176A (en) | 1942-12-18 | 1942-12-18 | Process for the preparation of an acylated, aliphatic aminocarboxamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH253176A (en) |
-
1942
- 1942-12-18 CH CH253176D patent/CH253176A/en unknown
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