CH267568A - 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
- CH267568A CH267568A CH267568DA CH267568A CH 267568 A CH267568 A CH 267568A CH 267568D A CH267568D A CH 267568DA CH 267568 A CH267568 A CH 267568A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- acid
- methyl
- formula
- dimethyl
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines cc,@-ungesättigten Carbonsäureamides. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines a,f-tuigesät- tigten Carbonsäureamides. Das Verfahren ist dadurch gekennzeichnet, dass man ein N-Alkyl- arylamin der Formel
EMI0001.0009
mit einer Verbindung der Formel CH,-CH =<B>CH</B> -COX umsetzt, wobei X und Y bei der Reaktion sich abspaltende Reste bedeuten.
Als N A1kyl-ary-l.- amine der Formel
EMI0001.0015
kommen das freie Amin bzw. seine Salze, Me tallverbindungen oder reaktionsfähigen Deri vate und als Verbindungen der Formel CH f-CI4 = CH -COX die freie Säure bzw. ihre reaktionsfähigen funktionellen Derivate, wie z. B. Halogenide, Anhydride, Ester, Ainide oder Salze, in Be tracht.
Eine spezielle Variante, die ebenfalls nach obigem Reaktionsschema verläuft, ist die Unisetzung von Salzen der Crotonsäure mit reaktionsfähigen Derivaten der N-Methyl-N- 3,4-dimethy 1-phenyl-carbaminsäure.
Die erhaltene neue Verbindung, das Cro- tonsätire-N-metliyl-3,4-dimethyl-anilid, stellt ein schwach gelbliches Öl dar, das unter 0,6 mm Druck bei 136 bis 1390 siedet, fungizid wirkt und als Mittel zur Insektenvergrämung dienen soll.
<I>Beispiel 1:</I> 10,5 Teile Crotonsäurechlorid werden unter Rühren so zu 27 Teilen N-Methyl-3,4-dimethyl- anilin 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 Croton- säure-N-inethyl-3,4-dimethylanilid siedet unter 0,6 mm Druck bei 136 bis 1390 und stellt ein schwach gelbliches Öl dar.
Statt in Gegenwart eines Überschusses an N-3,4-Trimethyl-anilin kann die Reaktion auch in Gegenwart eines säurebindenden Mittels, z. B. von Pottasche, durchgeführt werden, wo bei zweckmässig in einem Lösungsmittel, wie z. B. Aceton, gearbeitet wird.
<I>Beispiel 2:</I> Das trockene Natriumsalz der Crotonsäure wird zusammen mit der berechneten -Ienge Chlorameisensäure-N-Alethyl-3,4-dimethyl-ani- lid in einem geräumigen Kolben auf etwa 1800 erhitzt, bis die unter starkem Schäumen ver laufende Kohlendioxydentwicklung beendet ist. Man lässt auf etwa<B>1000</B> 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 Crotonsäure-N-methyl-3,4-dimethyl- anilid durch Destillieren im Vakuum gerei- Illgt. Es siedet unter 0,6 mm Druck bei 136 bis 1390.
Process for the preparation of a cc, @ - unsaturated carboxamide. The subject of the present patent is a process for the preparation of an α, f-tuigesät- saturated carboxamide. The process is characterized in that an N-alkylarylamine of the formula
EMI0001.0009
with a compound of the formula CH, -CH = <B> CH </B> -COX, where X and Y are radicals which are split off during the reaction.
As N-alkyl-ary-l-amines of the formula
EMI0001.0015
come the free amine or its salts, metal compounds or reactive derivatives and as compounds of the formula CH f-Cl4 = CH -COX 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 conversion of salts of crotonic acid with reactive derivatives of N-methyl-N-3,4-dimethyl-1-phenyl-carbamic acid.
The new compound obtained, the Crotonsätire-N-methyl-3,4-dimethyl-anilide, is a pale yellowish oil that boils at 136 to 1390 under 0.6 mm pressure, has a fungicidal effect and serves as an agent to deter insects should.
Example 1: 10.5 parts of crotonic acid chloride are added dropwise to 27 parts of N-methyl-3,4-dimethylaniline with stirring in such a way that the temperature rises to 130 to 1400. After cooling, the reaction product is dissolved in ether or another 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. Crotonic acid N-ynethyl-3,4-dimethylanilide boils under 0.6 mm pressure at 136 to 1390 and is a pale yellowish oil.
Instead of in the presence of an excess of N-3,4-trimethyl-aniline, the reaction can also be carried out in the presence of an acid-binding agent, e.g. B. of potash, where appropriate in a solvent, such as. B. acetone is worked.
<I> Example 2: </I> The dry sodium salt of crotonic acid is heated together with the calculated amount of chloroformic acid-N-Alethyl-3,4-dimethyl-anilide in a large flask to about 1800 until the under strong Foaming ver ongoing evolution of carbon dioxide has ended. Allow to cool to about <B> 1000 </B>, add hot water and boil for a short time.
After cooling, the product is taken up in ether, the solution is washed successively with dilute acid, water, dilute lye and then again with water. After drying with sodium sulfate, the ether is distilled off. The crotonic acid-N-methyl-3,4-dimethylanilide obtained as residue is then purified by distillation in vacuo. It boils under 0.6 mm pressure at 136 to 1390.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH257648T | 1946-06-28 | ||
CH267568T | 1946-06-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH267568A true CH267568A (en) | 1950-03-31 |
Family
ID=25730089
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH267568D CH267568A (en) | 1946-06-28 | 1946-06-28 | Process for the preparation of an α, B-unsaturated carboxamide. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH267568A (en) |
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1946
- 1946-06-28 CH CH267568D patent/CH267568A/en unknown
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