CH267564A - 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
CH267564A
CH267564A CH267564DA CH267564A CH 267564 A CH267564 A CH 267564A CH 267564D A CH267564D A CH 267564DA CH 267564 A CH267564 A CH 267564A
Authority
CH
Switzerland
Prior art keywords
ethyl
preparation
acid
formula
crotonic 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 CH267564A publication Critical patent/CH267564A/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,@.ungesättigten        Carbonsäureamides.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur Herstellung eines a,     l-ungesät-          tigten        Carbonsä        ureamides.    Das Verfahren ist  dadurch gekennzeichnet, dass man ein     N-Alky        l-          arylamin    der Formel  
EMI0001.0010     
    mit einer Verbindung der Formel         CH3-CH    =     CH-COX       umsetzt, wobei X und Y bei der Reaktion sich  abspaltende Reste bedeuten.

   Als     N-Alkyl-aryl-          amine    der Formel  
EMI0001.0015     
    kommen das freie Amin bzw. seine Salze, Me  tallverbindungen oder reaktionsfähigen Deri  vate, und als Verbindungen der Formel  '     CH3-CH    =     CH        -COX     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     Crotonsäure    mit  reaktionsfähigen Derivaten der     N-Äthyl-N-p-          tolyl-carbaminsäure.     



  Die erhaltene neue Verbindung, das     Cro-          tonsäure-N-äthyl-p-toluidid,    stellt ein schwach    gelbliches Öl dar, das unter 11 mm Druck bei  159 bis 1630 siedet,     fungizid    wirkt und als       Mittel    zur     Insektenvergrämung    dienen soll.  



  <I>Beispiel I:</I>  10,5 Teile     Crotonsäurechlorid    werden unter  Rühren so zu 27 Teilen     N-äthyl-p-toluidin    ge  tropft, dass die Temperatur auf 130 bis     140'3     steigt. Nach dem Erkalten     wird    das Reaktions  produkt in Äther oder einem andern mit Was  ser nicht mischbaren Lösungsmittel gelöst und  die Lösung nacheinander mit Salzsäure, Lauge  und Wasser gewaschen. Nach     Abdestillieren     des Lösungsmittels wird der Rückstand im     Va-          l@uum.    destilliert.

   Das     Crotonsäure-N-äthyl-p-          t.oluidid    siedet unter 11 mm Druck bei 159 bis       7.630    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.         Beispiel   <I>2:</I>  Das trockene     Natriumsalz    der     Cr        otonsäure     wird zusammen mit der berechneten Menge       Chlorameisensäure    - N -     äthyl    - p -     toluidid    in  einem geräumigen Kolben auf etwa 1800 er  hitzt, bis die unter starkem Schäumen verlau  fende Kohlendioxydentwicklung beendet ist.

    Man lässt auf etwa 1000 abkühlen, setzt heisses  Wasser zu und kocht kurze Zeit auf. Nach Er  kalten nimmt man das Produkt in Äther auf,      wäscht die     Lösung    nacheinander mit verdünn  ter Säure, Wasser, verdünnter Lauge und  hierauf wieder mit Wasser. Nach Trocknen  mit Natriumsulfat wird der Äther     abdestil-          liert.    Hierauf wird das als Rückstand erhal  tene     Crotonsäure-N-äthyl-p-toluidid    durch De  stillieren im Vakuum gereinigt. Es siedet un  ter 11     mm    Druck bei 159 bis 1631.



  Process for the preparation of an a, @. Unsaturated carboxamide. The subject of the present patent is a process for the preparation of an α, l-unsaturated carboxamide. The process is characterized in that an N-alkyl arylamine of the formula
EMI0001.0010
    with a compound of the formula CH3-CH = CH-COX, where X and Y are radicals which are split off during the reaction.

   As N-alkyl-aryl amines of the formula
EMI0001.0015
    come the free amine or its salts, metal compounds or reactive derivatives, and as compounds of the formula 'CH3-CH = CH -COX 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 crotonic acid with reactive derivatives of N-ethyl-N-p-tolyl-carbamic acid.



  The new compound obtained, the crotonic acid-N-ethyl-p-toluidide, is a pale yellowish oil that boils at 159 to 1630 under 11 mm pressure, has a fungicidal effect and is intended to serve as a deterrent to insects.



  <I> Example I: </I> 10.5 parts of crotonic 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 140-3. After cooling, the reaction product is dissolved in ether or another solvent which is 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 in Va- l @ uum. distilled.

   The crotonic acid-N-ethyl-p-t.oluidide boils under 11 mm pressure at 159 to 7,630 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. Example <I> 2: </I> The dry sodium salt of crotonic acid is heated together with the calculated amount of chloroformic acid - N - ethyl - p - toluidide in a spacious flask to about 1,800 until the evolution of carbon dioxide, which is accompanied by strong foaming, ceases is.

    Allow to cool to about 1000, add hot water and boil for a short time. After cold, the product is taken 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 crotonic acid-N-ethyl-p-toluidide obtained as a residue is then purified by distillation in vacuo. It boils under 11 mm pressure at 159 to 1631.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines a,ss-un- gesättigten Carbonsäureamides, dadurch ge kennzeichnet, dass man ein N-Alkyl-arylamin der Formel EMI0002.0010 mit. einer Verbindung der Formel CH3-CH = CH-CON umsetzt, wobei N und Y bei der Reaktion sich abspaltende Reste bedeuten. Die erhaltene neue Verbindung, das Crotonsä.ure-N-äthyl-p- toluidid, stellt ein schwach gelbliches Öl dar, das unter 1l mm Druck bei 159 bis 1630 siedet. PATENT CLAIM Process for the preparation of an α, β-unsaturated carboxamide, characterized in that an N-alkyl-arylamine of the formula EMI0002.0010 With. a compound of the formula CH3-CH = CH-CON, where N and Y are radicals which are split off during the reaction. The new compound obtained, crotonic acid-N-ethyl-p-toluidide, is a pale yellowish oil that boils at 159 to 1630 under 11 mm pressure. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass ein Salz der Crotonsäure mit einem reaktionsfähigen Halogenid der N- Äthyl-N-p-tolyl-carbaminsäure umgesetzt v ir d. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that a salt of crotonic acid is reacted with a reactive halide of N-ethyl-N-p-tolyl-carbamic acid v ir d.
CH267564D 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide. CH267564A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH267565T 1946-06-28
CH257648T 1946-06-28
CH267564T 1946-06-28

Publications (1)

Publication Number Publication Date
CH267564A true CH267564A (en) 1950-03-31

Family

ID=27178076

Family Applications (1)

Application Number Title Priority Date Filing Date
CH267564D CH267564A (en) 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide.

Country Status (1)

Country Link
CH (1) CH267564A (en)

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