CH267576A - 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
CH267576A
CH267576A CH267576DA CH267576A CH 267576 A CH267576 A CH 267576A CH 267576D A CH267576D A CH 267576DA CH 267576 A CH267576 A CH 267576A
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 CH267576A publication Critical patent/CH267576A/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          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  
EMI0001.0011     
    mit einer Verbindung der Formel  
EMI0001.0012     
    umsetzt, wobei X und Y bei der Reaktion sich  abspaltende Reste bedeuten.

   Als     N-Alkyl-aryl-          a.mine    der Formel  
EMI0001.0015     
    kommen das freie Amin bzw. seine Salze, Me  tallverbindungen oder reaktionsfähigen Deri  vate und als Verbindungen der Formel  
EMI0001.0016     
    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  Äthyl-N-o-tolyl-carbaminsäure.

    



  Die erhaltene neue Verbindung, das     Tri-          methylaerylsäure-N-äthyl-o-toluidid,    stellt ein  schwach gelbliches öl dar, das unter 12 mm  Druck bei 152 bis 1560 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-Äthyl-o-          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-          methylacrylsäure-N-äthyl-o-toluidid    siedet un  ter 12 mm Druck bei 152 bis 1560 und stellt  ein schwach gelbliches öl dar.  



  Statt in Gegenwart: eines Überschusses an       N-Äthyl-o-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.  



       Beispiel   <I>2:</I>  Das trockene     Natriumsalz    der     Trimethyl-          acrylsäure    wird zusammen mit der berechne-           ten    Menge     Chlorameisensäure-N-äthyl-o-t.olui-          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     Trimet.hylacrylsäure-N-äthyl-o-tolui-          did    durch Destillieren im Vakuum gereinigt.  Es siedet unter 12 mm Druck bei 152 bis 1560.



      Process for the preparation of a 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
EMI0001.0011
    with a compound of the formula
EMI0001.0012
    converts, where X and Y are radicals which are split off during the reaction.

   As N-alkyl-aryl a.mine of the formula
EMI0001.0015
    come the free amine or its salts, metal compounds or reactive derivatives and as compounds of the formula
EMI0001.0016
    the free acid or its reactive functional derivatives, such as. B. halides, anhydrides, esters, amides or salts, into consideration. 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-ethyl-N-o-tolyl-carbamic acid.

    



  The new compound obtained, the trimethylaeryl acid-N-ethyl-o-toluidide, is a pale yellowish oil that boils at 152 to 1560 under 12 mm pressure, has a fungicidal effect 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-o-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 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. The trimethyl acrylic acid-N-ethyl-o-toluidide boils under 12 mm pressure at 152 to 1560 and is a pale yellowish oil.



  Instead of in the presence: an excess of N-ethyl-o-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.



       Example <I> 2: </I> The dry sodium salt of trimethyl acrylic acid is heated together with the calculated amount of chloroformic acid-N-ethyl-ot.oluid in a spacious flask to about 1800 until the with strong foaming The evolution of carbon dioxide has ended .. Allow to cool to about 1000, 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 trimet.hylacrylic acid-N-ethyl-o-toluidide obtained as residue is then purified by distillation in vacuo. It boils under 12 mm of pressure at 152 to 1560.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines a,ss-un- gesättigten Carbonsäureamides, dadurch ge kennzeichnet., dass man ein N-Alkyl-arylamin der Formel EMI0002.0014 mit einer Verbindung der Formel EMI0002.0016 umsetzt, wobei X und Y bei der Reaktion sieh abspaltende Reste bedeuten. Die erhaltene neue Verbindung, das Trimethyl-acrylsäure-N- äthyl-o-toluidid, stellt: ein sehwach gelbliches öl dar, das unter 12 mm Druck bei 152 bis 1560 siedet:. PATENT CLAIM: A process for the preparation of an α, β-unsaturated carboxamide, characterized in that an N-alkyl-arylamine of the formula EMI0002.0014 with a compound of the formula EMI0002.0016 reacted, where X and Y in the reaction are separating radicals. The new compound obtained, the trimethyl-acrylic acid-N-ethyl-o-toluidide, is: a weakly yellowish oil which boils under 12 mm pressure at 152 to 1560 :. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass ein Salz der Trimethyl- acrylsäure mit einem reaktionsfähigen Halo genid der N-Äthyl-N-o-tolyl-earbaminsäure umgesetzt, wird. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that a salt of trimethyl acrylic acid is reacted with a reactive halide of N-ethyl-N-o-tolyl-earbamic acid.
CH267576D 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide. CH267576A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH257648T 1946-06-28
CH267576T 1946-06-28

Publications (1)

Publication Number Publication Date
CH267576A true CH267576A (en) 1950-03-31

Family

ID=25730097

Family Applications (1)

Application Number Title Priority Date Filing Date
CH267576D CH267576A (en) 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide.

Country Status (1)

Country Link
CH (1) CH267576A (en)

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