CH267578A - 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
CH267578A
CH267578A CH267578DA CH267578A CH 267578 A CH267578 A CH 267578A CH 267578D A CH267578D A CH 267578DA CH 267578 A CH267578 A CH 267578A
Authority
CH
Switzerland
Prior art keywords
acid
preparation
formula
methyl
unsaturated carboxamide
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 CH267578A publication Critical patent/CH267578A/en

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     a,i3-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  
EMI0001.0013     
    kommen das freie Amin bzw. seine Salze, Me  tallverbindungen oder reaktionsfähigen Deri  vate und als Verbindungen der Formel  
EMI0001.0014     
    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     Trimethylacryl-          säure    mit reaktionsfähigen Derivaten der N  Methyl-N-p-tolyl-carbaminsäure.  



  Die erhaltene neue Verbindung, das     Tri-          methylacrylsäure-N-methyl-p-toluidid,    stellt  ein schwach gelbliches öl dar, das unter 12     mm     Druck bei 153 bis 1570 siedet,     fungizid    wirkt  und als Mittel zur     Insektenvergrämung    dienen  soll.  



  <I>Beispiel 1:</I>  13,3 Teile     Trimethylacrylsäurechlorid    wer  den unter Rühren so     ztt    24,2 Teilen     N-Methyl-          p-toluidin    getropft, dass die Temperatur auf  130 bis 1400 steigt. Nach dem Erkalten wird  das Reaktionsprodukt in Äther oder einem an  dern 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     Tri-          methylacrylsäure-N-methyl-p-toluidid    siedet  unter 12 mm Druck bei 153 bis 1570 und stellt  ein schwach gelbliches öl dar.  



  Statt in Gegenwart eines Überschusses an       N-Methyl-p-toluidin    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     Trimethyl-          acrylsäure    wird zusammen mit der berechne-           ten    Menge     Chlorameisensäure-N-methyl-p-to-          luidid    in einem geräumigen Kolben auf etwa  1800 erhitzt, bis die unter starkem Schäumen  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     Trimethylacrylsäure-N-methyl-p-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, i3-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
EMI0001.0013
    come the free amine or its salts, metal compounds or reactive derivatives and as compounds of the formula
EMI0001.0014
    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 trimethylacrylic acid with reactive derivatives of N-methyl-N-p-tolyl-carbamic acid.



  The new compound obtained, the trimethyl acrylic acid-N-methyl-p-toluidide, is a pale yellowish oil that boils at 153 to 1570 under 12 mm pressure, has a fungicidal effect and is intended to serve as a deterrent to insects.



  <I> Example 1: </I> 13.3 parts of trimethylacrylic acid chloride are added dropwise to 24.2 parts of N-methyl-p-toluidine while stirring that the temperature rises to 130 to 1400. After cooling, the reaction product is dissolved in ether or another solvent immiscible with: water 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 trimethyl acrylic acid-N-methyl-p-toluidide boils under 12 mm pressure at 153 to 1570 and is a pale yellowish oil.



  Instead of in the presence of an excess of N-methyl-p-toluidine, the reaction can also be carried out in the presence; 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 trimethyl acrylic acid is heated together with the calculated amount of chloroformic acid-N-methyl-p-toluidide in a spacious flask to about 1800 until the under strong foaming ongoing evolution of carbon dioxide has ended. One lets on about. 1000 cool, 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 trimethylacrylic acid-N-methyl-p-toluidide obtained as residue is then purified by distillation in vacuo. It boils under 12 mm of pressure at 153 to 1570.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines a,ss-un- gesättigten Carbonsäureamides, dadurch ge kennzeichnet, dass man ein N-Alkyl-arylamin der Formel EMI0002.0017 mit: einer Verbindung der Formel EMI0002.0018 umsetzt, wobei X und Y bei der Reaktion sich abspaltende Reste bedeuten. Die erhaltene neue Verbindung, das Trimethylacrylsäure-N- methyl-p-toluidid, stellt ein sehwaeh gelbliches Öl dar, das unter 12 mm Druck bei 153 bis 1.570 siedet. PATENT CLAIM: Process for the preparation of an α, β-unsaturated carboxamide, characterized in that an N-alkyl-arylamine of the formula EMI0002.0017 with: a compound of the formula EMI0002.0018 converts, where X and Y are radicals which are split off during the reaction. The new compound obtained, trimethylacrylic acid-N-methyl-p-toluidide, is a slightly yellowish oil that boils at 153 to 1570 under 12 mm pressure. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass ein Salz der Trimethyl- acrylsäure mit einem reaktionsfähigen Halo genid der N-lIethyl-N-p-tolyl-carbaminsäure umgesetzt wird. SUBSTITUTE SHEET: Process according to claim, characterized in that a salt of trimethyl acrylic acid is reacted with a reactive halide of N-ethyl-N-p-tolyl-carbamic acid.
CH267578D 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide. CH267578A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH257648T 1946-06-28
CH267578T 1946-06-28

Publications (1)

Publication Number Publication Date
CH267578A true CH267578A (en) 1950-03-31

Family

ID=25730099

Family Applications (1)

Application Number Title Priority Date Filing Date
CH267578D CH267578A (en) 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide.

Country Status (1)

Country Link
CH (1) CH267578A (en)

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