CH267569A - 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
CH267569A
CH267569A CH267569DA CH267569A CH 267569 A CH267569 A CH 267569A CH 267569D A CH267569D A CH 267569DA CH 267569 A CH267569 A CH 267569A
Authority
CH
Switzerland
Prior art keywords
acid
methyl
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 CH267569A publication Critical patent/CH267569A/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

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,9-ungesättigten        Carbonsäureamides.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur Herstellung eines     a,ss-ungesät-          iigten        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-          a.mine    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-          acrylsäure    mit reaktionsfähigen Derivaten der       N-Methyl-N-o-tolyl-carbaminsäure.     



  Die erhaltene neue Verbindung, das     Di-          methylacrylsäure-N-methyl-o-toluidid,    stellt  ein schwach gelbliches öl dar, das unter 12 mm  Druck bei 145 bis 1500 siedet,     fungizid    wirkt  und als Mittel zur     Insektenvergrämung    dienen  soll.  



  <I>Beispiel 1:</I>  11,9 Teile     ss,ss-Dimethyl-acrylsäurechlorid     werden unter Rühren so zu 24,2 Teilen     N-Me-          thyl-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 nachein  ander mit Salzsäure, Lauge und Wasser ge  waschen. Nach     Abdestillieren    des Lösungsmit  tels wird der Rückstand im Vakuum destil  liert. Das     Dimethylacrylsäure-N-methyl-o-to-          luidid    siedet unter 12 mm Druck bei 145 bis  1500 und stellt ein schwach gelbliches öl dar.  



  Statt in Gegenwart eine Überschusses an       N-Methyl-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.  



  <I>Beispiel 2:</I>  Das trockene     Natriumsalz    der     ss,ss-Dimethyl-          a.crylsäure    wird zusammen mit der berechne-           ten    Menge     Chlorameisensäure-N-methyl-o-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     Dimethylacrylsäure-N-methyl-o-to-          luidid    durch Destillieren im Vakuum gerei  nigt. Es siedet unter 12 mm Druck bei 145 bis  1500.



  Process for the preparation of an α, 9-unsaturated carboxamide. The present patent relates to a process for the preparation of an α, β-unsaturated carboxamide. The procedure is. characterized in that an N-alkyl arylamine 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 a.mine 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-methyl-N-o-tolyl-carbamic acid.



  The new compound obtained, dimethyl acrylic acid-N-methyl-o-toluidide, is a pale yellowish oil that boils at 145 to 1500 under 12 mm pressure, has a fungicidal effect and is intended to serve as a deterrent to insects.



  Example 1: 11.9 parts of SS, SS-dimethyl-acrylic acid chloride are added dropwise to 24.2 parts of N-methyl-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 in succession with hydrochloric acid, alkali and water. After the solvent has been distilled off, the residue is distilled in vacuo. The dimethylacrylic acid-N-methyl-o-toluidide boils under 12 mm pressure at 145 to 1500 and is a pale yellowish oil.



  Instead of an excess of N-methyl-o-toluidine in the presence of, the reaction can also be carried out in the presence; 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 to about 1800 in a large flask together with the calculated amount of chloroformic acid-N-methyl-o-toluidide until the evolution of carbon dioxide, which continues with vigorous foaming, 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 dimethylacrylic acid-N-methyl-o-toluidide obtained as residue is then purified by distillation in vacuo. It boils under 12 mm pressure at 145 to 1500.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines a,ss-un- gesättigten Carbonsäureamides, dadurch ge kennzeichnet, dass man ein N-Alkyl-arylamin der Formel EMI0002.0013 mit. einer Verbindung der Formel EMI0002.0014 umsetzt, wobei X und Y bei der Reaktion sich abspaltende Reste bedeuten. Die erhaltene neue Verbindung, das Dimethylacrylsäure-N- methyl-o-toluidid, stellt. ein schwach gelbliches Öl dar, das unter 12 mm Druck bei 145 bis 1500 siedet. PATENT CLAIM: Process for the preparation of an α, β-unsaturated carboxamide, characterized in that an N-alkyl-arylamine of the formula EMI0002.0013 With. a compound of the formula EMI0002.0014 converts, where X and Y are radicals which are split off during the reaction. The new compound obtained, dimethylacrylic acid-N-methyl-o-toluidide, provides. is a pale yellowish oil that boils at 145 to 1500 under 12 mm pressure. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass ein Salz der ss,ss-Dimethyl- acrylsäure mit einem reaktionsfähigen Halo genid der N-Methyl-N-o-tolylcarbaminsäure umgesetzt wird. SUBCLAIM: Process according to claim, characterized in that a salt of ss, ss-dimethyl acrylic acid is reacted with a reactive halide of N-methyl-N-o-tolylcarbamic acid.
CH267569D 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide. CH267569A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH267569T 1946-06-28
CH257648T 1946-06-28

Publications (1)

Publication Number Publication Date
CH267569A true CH267569A (en) 1950-03-31

Family

ID=25730090

Family Applications (1)

Application Number Title Priority Date Filing Date
CH267569D CH267569A (en) 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide.

Country Status (1)

Country Link
CH (1) CH267569A (en)

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