CH264488A - Process for the preparation of an acyl derivative of an acetoacetic acid amide. - Google Patents
Process for the preparation of an acyl derivative of an acetoacetic acid amide.Info
- Publication number
- CH264488A CH264488A CH264488DA CH264488A CH 264488 A CH264488 A CH 264488A CH 264488D A CH264488D A CH 264488DA CH 264488 A CH264488 A CH 264488A
- Authority
- CH
- Switzerland
- Prior art keywords
- chloro
- acid amide
- preparation
- acetoacetic acid
- acyl derivative
- Prior art date
Links
Description
Verfahren zur <B>Herstellung eines</B> Acylderivates <B>eines</B> Acetessigsäureamides. Es wurde gefunden, dass ein neues Acyl- derivat eines Acetessigsäureamides hergestellt werden kann, wenn man auf 2 Mol einer Al kalimetallverbindung des 1-Acetoacetylamino- 2-chlor-benzols 1 Mol p-Chlor-benzoylehlorid einwirken lässt.
Das gebildete Acetyl-p-chlor-benzoyl-essig- säure-o-chlor-anilid stellt in getrocknetem Zu stande ein weisses kristallines Pulver dar und ist ein wertvolles Zwischenprodukt für die Herstellung von Azofarbstoffen.
Beispiel: 211,5 Teile Acetessigsäure-o-ehlor-anilid werden mit 105 Raumteilen Natronlauge 360 B6 (1 Mol + 5 % ) in 1000 Teilen Wasser bei 400 gelöst, die Lösung von Verunreinigun gen abfiltriert und auf 0 bis 50 gekühlt. Un ter gutem Rühren lässt man innerhalb 30 Mi nuten 88 Teile p-Chlor-benzoylchlorid zuflie ssen.
Man rührt 2 bis 3 Stunden bei 50, setzt dann 52 Raumteile Natronlauge zu und lässt wieder in 30 Minuten 44 Teile p-Chlor-ben- zoylchlorid zufliessen und rührt 2 Stunden. Diese Operation wiederholt. man jeweils mit der Hälfte der vorher verwendeten Mengen Lauge und Chlorid, bis im ganzen 176 Teile p-Chlor-benzoylchlorid verbraucht wurden. Dann rührt man weitere 12 Stunden unter Kühlung auf 50 und filtriert dann die Lösung von geringen Mengen unlöslicher Rückstände ab.
Die klare Lösung wird mit 150 Raumteilen konzentrierter Salzsäure versetzt, wobei sich das Kondensationsprodukt als weisse Fällung, die nach kurzer Zeit kristalliniseh erstarrt, ab scheidet. Man rührt noch etwa 1 Stunde bei Raumtemperatur, filtriert und wäscht mit Wasser. Nach dem Trocknen im Vakuiun er hält man das Kondensationsprodukt in einer Ausbeute von 290 bis 300 Teilen als weisses kristallines Pulver.
Process for the <B> production of </B> an acyl derivative <B> of </B> acetoacetic acid amide. It has been found that a new acyl derivative of an acetoacetic acid amide can be prepared if 1 mole of p-chloro-benzoylechloride is allowed to act on 2 moles of an alkali metal compound of 1-acetoacetylamino-2-chlorobenzene.
The acetyl-p-chloro-benzoyl-acetic acid-o-chloro-anilide that is formed is a white crystalline powder when dried and is a valuable intermediate product for the production of azo dyes.
Example: 211.5 parts of acetoacetic acid-o-chloro-anilide are dissolved with 105 parts by volume of sodium hydroxide solution 360 B6 (1 mol + 5%) in 1000 parts of water at 400, the solution of impurities is filtered off and cooled to 0 to 50. With thorough stirring, 88 parts of p-chloro-benzoyl chloride are allowed to flow in within 30 minutes.
The mixture is stirred for 2 to 3 hours at 50, then 52 parts by volume of sodium hydroxide solution are added and 44 parts of p-chloro-benzoyl chloride are allowed to flow in again in 30 minutes and the mixture is stirred for 2 hours. Repeated this operation. one with half of the previously used amounts of alkali and chloride until a total of 176 parts of p-chloro-benzoyl chloride have been consumed. The mixture is then stirred for a further 12 hours while cooling to 50 and the solution is then filtered to remove small amounts of insoluble residues.
The clear solution is mixed with 150 parts by volume of concentrated hydrochloric acid, the condensation product separating out as a white precipitate which solidifies in crystalline form after a short time. The mixture is stirred for about 1 hour at room temperature, filtered and washed with water. After drying in a vacuum, the condensation product is kept in a yield of 290 to 300 parts as a white crystalline powder.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH258583T | 1946-07-30 | ||
| CH264488T | 1947-05-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH264488A true CH264488A (en) | 1949-10-15 |
Family
ID=25730180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH264488D CH264488A (en) | 1946-07-30 | 1947-05-23 | Process for the preparation of an acyl derivative of an acetoacetic acid amide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH264488A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2700037A (en) * | 1949-05-03 | 1955-01-18 | Ciba Ltd | Process for the manufacture of monoacyl acetyl compounds of primary amines |
-
1947
- 1947-05-23 CH CH264488D patent/CH264488A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2700037A (en) * | 1949-05-03 | 1955-01-18 | Ciba Ltd | Process for the manufacture of monoacyl acetyl compounds of primary amines |
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