CH267572A - Process for the preparation of an α, B-unsaturated carboxamide. - Google Patents

Process for the preparation of an α, B-unsaturated carboxamide.

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Publication number
CH267572A
CH267572A CH267572DA CH267572A CH 267572 A CH267572 A CH 267572A CH 267572D A CH267572D A CH 267572DA CH 267572 A CH267572 A CH 267572A
Authority
CH
Switzerland
Prior art keywords
ethyl
preparation
acid
formula
acrylic acid
Prior art date
Application number
Other languages
German (de)
Inventor
Ag J R Geigy
Original Assignee
Ag J R Geigy
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ag J R Geigy filed Critical Ag J R Geigy
Publication of CH267572A publication Critical patent/CH267572A/en

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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

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  • 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     a,ss#ungesättigten        Carbonsäureamides.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur Herstellung eines     a,ss-ungesät-          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 ss,ss-Dimethyl-acryl-    säure mit reaktionsfähigen Derivaten der     N-          Ä        thyl-N-p-tolyl-carbaminsäure.     



  Die erhaltene neue Verbindung, das     Di-          methylacrylsäure-N-äthyl-p-toluidid,    stellt ein.  schwach gelbliches Öl dar, das unter 11 mm  Druck bei 160 bis 163  siedet, Fungizid wirbt  und als Mittel zur     Insektenvergrämung    dienen  soll.  



  <I>Beispiel Z:</I>  11,9 Teile     ss,ss-Dimethyl-acrylsäurechlorid     werden unter Rühren so zu 27 Teilen     N-Äthyl-          p-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 Lösungs  mittel gelöst und die Lösung nacheinander mit  Salzsäure, Lauge und Wasser gewaschen.  Nach     Abdestillieren    des Lösungsmittels wird  der Rückstand im Vakuum destilliert. Das     Di-          methyl-acrylsäure-N-äthyl-p-toluidid    siedet  unter 11 mm Druck bei 160 bis 1630 und stellt  ein schwach gelbliches Öl dar.  



  Statt in Gegenwart eines Überschusses an       N-Äthyl-p-toluidin    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     ss,ss-Di-          methylacrylsäure    wird zusammen mit der be  rechneten Menge     Chlorameisensäure-N-äthyl-,              p-toluidid    in einem geräumigen Kolben auf  etwa 1800 erhitzt, bis die unter starkem Schäu  men verlaufende 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     Dimethyl-acrylsäure-N-äthyl-p-to-          luidid    durch Destillieren im Vakuum gerei  nigt. Es siedet     Liter    11 mm Druck bei 160 bis  1630.



  Process for the preparation of an a, ss # unsaturated carboxamide. The present patent relates to a process for the preparation of an α, β-unsaturated 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 ß, ß-dimethyl-acrylic acid with reactive derivatives of N-ethyl-N-p-tolyl-carbamic acid.



  The new compound obtained, dimethyl acrylic acid-N-ethyl-p-toluidide, ceases. slightly yellowish oil, which boils at 160 to 163 under 11 mm pressure, advertises fungicide and is said to serve as a means to deter insects.



  <I> Example Z: </I> 11.9 parts of SS, SS-dimethyl-acrylic acid chloride are added dropwise to 27 parts of N-ethyl-p-toluidine with stirring in such a way that the temperature rises to 130 to 1400. After cooling, the reaction product is dissolved in ether or some other 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 dimethyl-acrylic acid-N-ethyl-p-toluidide boils under 11 mm pressure at 160 to 1630 and is a pale yellowish oil.



  Instead of in the presence of an excess of N-ethyl-p-toluidine, the reaction can also be carried out in the presence of an acid-binding agent, e.g. B. of potash, be carried out, advantageously in a solvent such. B. acetone, is worked.



  <I> Example 2: </I> The dry sodium salt of ss, ss-dimethyl acrylic acid is heated together with the calculated amount of chloroformic acid-N-ethyl-, p-toluidide in a large flask to about 1800 until the below the development of carbon dioxide has ceased. Allow to cool to about 1000, add hot water and boil for a short time. After cooling, 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 dimethyl-acrylic acid-N-ethyl-p-toluidide obtained as residue is then purified by distillation in vacuo. It boils liters of 11 mm pressure at 160 to 1630.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines a,f un gesättigten Carbonsäureamides, dadurch ge kennzeichnet, dass man ein N-Alkyl-arylamin der Formel EMI0002.0009 mit einer Verbindung der Formel EMI0002.0010 umsetzt; wobei X und Y bei der Reaktion sich abspaltende Reste bedeuten. Die erhaltene neue Verbindung, das Dimethylacrylsäure-N- äthyl-p-toluidid, stellt ein schwach gelbliches öl dar, das unter 11 mm Druck bei 160 bis <B>1.630</B> siedet. PATENT CLAIM: Process for the preparation of an a, f un saturated carboxamide, characterized in that an N-alkyl-arylamine of the formula EMI0002.0009 with a compound of the formula EMI0002.0010 implements; where X and Y denote radicals which split off during the reaction. The new compound obtained, dimethylacrylic acid-N-ethyl-p-toluidide, is a pale yellowish oil that boils at 160 to 1.630 under 11 mm pressure. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass ein Salz der f,fl-Dimethyl- acrylsäure mit einem reaktionsfähigen Halo genid der N-Äthyl-N-p-toly l-carbaminsäure umgesetzt wird. SUBCLAIM: Process according to claim, characterized in that a salt of f, fl-dimethyl acrylic acid is reacted with a reactive halide of N-ethyl-N-p-toly l-carbamic acid.
CH267572D 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide. CH267572A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH257648T 1946-06-28
CH267572T 1946-06-28

Publications (1)

Publication Number Publication Date
CH267572A true CH267572A (en) 1950-03-31

Family

ID=25730093

Family Applications (1)

Application Number Title Priority Date Filing Date
CH267572D CH267572A (en) 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide.

Country Status (1)

Country Link
CH (1) CH267572A (en)

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