CH267577A - Process for the preparation of an α, B-unsaturated carboxamide. - Google Patents
Process for the preparation of an α, B-unsaturated carboxamide.Info
- Publication number
- CH267577A CH267577A CH267577DA CH267577A CH 267577 A CH267577 A CH 267577A CH 267577D A CH267577D A CH 267577DA CH 267577 A CH267577 A CH 267577A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- ethyl
- preparation
- formula
- unsaturated carboxamide
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines a,@-ungesättigten Carbonsäureamides. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines a,fl'-tingesät- tigten Carbonsäureamides. Das Verfahren ist dadurch gekennzeichnet, dass man ein N-Alkyl- arylamin der Formel
EMI0001.0008
mit einer Verbindung der Formel
EMI0001.0009
umsetzt, wobei X und Y bei der Reaktion sich abspaltende Reste bedeuten.
Als N-Alkyl-aryl- amine der Formel
EMI0001.0012
kommen das freie Amin bzw. seine Salze, Me tallverbindungen oder reaktionsfähigen Deri vate und als Verbindungen der Formel
EMI0001.0013
die freie Säure bzw. ihre reaktionsfähigen funktionellen Derivate, wie z. B. Halogenide, Anhydride, Ester, Amide oder Salze, in Be tracht.
Eine spezielle Variante, die ebenfalls nach obigem Reaktionsschema verläuft, ist die Umsetzung von Salzen der Trimethy lacryl- säure mit reaktionsfähigen Derivaten der \T- Äthyl-N-m-toly l.-earbaminsäure.
Die erhaltene neue Verbindung, das Tri- methylacry lsäur e-N-äthyl-m-toluidid, stellt ein schwach gelbliches Öl dar, das unter 12 mm Druck bei 153 bis 157 siedet, Fungizid wirkt und als Mittel zur Insektenvergrämung dienen soll.
Beispiel <I>1:</I> 13,3 Teile Trimethylacrylsäurechlorid wer den unter Rühren so zu 27 Teilen N-Äthy 1-m- toluidin getropft, dass die Temperatur auf 130 bis 1400 steigt. Nach dem Erkalten wird das Reaktionsprodukt in Äther oder einem andern mit: Wasser nicht mischbaren Lösungsmittel gelöst und die Lösung nacheinander mit Salz säure, Lauge und Wasser gewaschen. Nach Abdestillieren des Lösungsmittels wird der Rückstand im Vakuum destilliert.
Das Tri- inethylacrylsätire-N-äthyl-m-toluidid siedet unter 12 mm Druck bei 153 bis 157 und stellt ein schwach gelbliches Öl dar. Statt in Gegenwart eines Überschusses an N-Äthyl-m-t:oluidin kann die Reaktion auch in Gegenwart eines säurebindenden Mittels, z. B. von Pottasche, durchgeführt: werden, wobei zweckmässig in einem Lösungsmittel, wie z. B. Aceton, gearbeitet wird.
<I>Beispiel 2:</I> Das trockene Natriumsalz der Trimethyl- acrylsäure wird zusammen mit der berechne ten Menge Chlorameisensäure N-äthyl-m-tolui- did in einem geräumigen Kolben auf etwa 1800 erhitzt, bis die unter starkem Schäumen ver laufende Kohlendioxydentwicklung beendet ist. Man lässt auf etwa 1000 abkühlen, setzt heisses Wasser zu und kocht kurze Zeit auf. Nach Erkalten nimmt; man das Produkt in Äther auf, wäscht die Lösung nacheinander mit verdünnter Säure, Wasser, verdünnter Lauge und hierauf wieder mit Wasser.
Nach Trocknen mit Natriumsulfat wird der Äther abdestilliert. Hierauf wird das als Rückstand erhaltene Trimethylacrylsäure-N-äthyl-m-to- luidid durch Destillieren im Vakuum gerei nigt. Es siedet unter 12 mm Druck bei 153 bis 1570.
Process for the preparation of an α, @ - unsaturated carboxamide. The subject of the present patent is a process for the preparation of an α, fl'-tingesaturated carboxamide. The process is characterized in that an N-alkylarylamine of the formula
EMI0001.0008
with a compound of the formula
EMI0001.0009
converts, where X and Y are radicals which are split off during the reaction.
As N-alkyl-aryl amines of the formula
EMI0001.0012
come the free amine or its salts, metal compounds or reactive derivatives and as compounds of the formula
EMI0001.0013
the free acid or its reactive functional derivatives, such as. B. halides, anhydrides, esters, amides or salts, in Be tracht.
A special variant, which also proceeds according to the above reaction scheme, is the reaction of salts of trimethyl acrylic acid with reactive derivatives of \ T-ethyl-N-m-tolyl-earbamic acid.
The new compound obtained, trimethylacrylic acid e-N-ethyl-m-toluidide, is a pale yellowish oil that boils at 153 to 157 under 12 mm pressure, has a fungicide and is intended to serve as a deterrent to insects.
Example <I> 1 </I> 13.3 parts of trimethylacrylic acid chloride are added dropwise to 27 parts of N-ethyl 1-m-toluidine with stirring so that the temperature rises to 130 to 1400. After cooling, the reaction product is dissolved in ether or another with: water-immiscible solvent and the solution is washed successively with hydrochloric acid, alkali and water. After the solvent has been distilled off, the residue is distilled in vacuo.
The Tri- inethylacrylsätire-N-ethyl-m-toluidid boils under 12 mm pressure at 153 to 157 and is a pale yellowish oil. Instead of in the presence of an excess of N-ethyl-mt: oluidine, the reaction can also be carried out in the presence of an acid-binding agent By means of e.g. B. of potash carried out: are, advantageously in a solvent, such as. B. acetone, is worked.
<I> Example 2: </I> The dry sodium salt of trimethyl acrylic acid is heated together with the calculated amount of chloroformic acid N-ethyl-m-toluidide in a spacious flask to about 1800 until it is heated with strong foaming Development of carbon dioxide has ended. Allow to cool to about 1000, add hot water and boil for a short time. After cooling down, takes; the product is washed up in ether, the solution is washed successively with dilute acid, water, dilute alkali and then again with water.
After drying with sodium sulfate, the ether is distilled off. The trimethylacrylic acid-N-ethyl-m-toluidide obtained as residue is then purified by distillation in vacuo. It boils under 12 mm of pressure at 153 to 1570.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH257648T | 1946-06-28 | ||
CH267577T | 1946-06-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH267577A true CH267577A (en) | 1950-03-31 |
Family
ID=25730098
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH267577D CH267577A (en) | 1946-06-28 | 1946-06-28 | Process for the preparation of an α, B-unsaturated carboxamide. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH267577A (en) |
-
1946
- 1946-06-28 CH CH267577D patent/CH267577A/en unknown
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