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
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 CH267577A publication Critical patent/CH267577A/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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  • 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)

PATENTANSPRUCH: Verfahren zur Herstellung eines a,ss-un- gesättigten Carbonsäureamides, dadurch ge kennzeichnet, dass man ein N-Alkyl-arylamin der Formel EMI0002.0016 mit einer Verbindung der Formel EMI0002.0017 umsetzt, wobei X und Y bei der Reaktion sich abspaltende Reste bedeuten. Die erhaltene neue Verbindung, das Trimethylacrylsäure-N- äthyl-m-toluidid, stellt ein schwach gelbliches Öl dar, das untrer 12 mm Druck bei 153 bis 1570 siedet. PATENT CLAIM: Process for the preparation of an α, β-unsaturated carboxamide, characterized in that an N-alkyl-arylamine of the formula EMI0002.0016 with a compound of the formula EMI0002.0017 converts, where X and Y are radicals which are split off during the reaction. The new compound obtained, the trimethylacrylic acid-N-ethyl-m-toluidide, is a pale yellowish oil which boils at 153 to 1570 under 12 mm pressure. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass ein Salz der Trimethy 1 acryisäure mit einem reaktionsfähigen Halo genid der N-Äthyl-N-m-tolyl-carbaminsäure umgesetzt wird. SUBSTANTIAL CLAIM: Process according to claim, characterized in that a salt of trimethyl acrylic acid is reacted with a reactive halide of N-ethyl-N-m-tolyl-carbamic acid.
CH267577D 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide. CH267577A (en)

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)

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