CH267563A - 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
CH267563A
CH267563A CH267563DA CH267563A CH 267563 A CH267563 A CH 267563A CH 267563D A CH267563D A CH 267563DA CH 267563 A CH267563 A CH 267563A
Authority
CH
Switzerland
Prior art keywords
methyl
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 CH267563A publication Critical patent/CH267563A/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,ss-ungesät-          tigten        Carbonsäureamides.    Das Verfahren ist  dadurch gekennzeichnet, dass man ein N     Alkyl-          arylamin    der Formel  
EMI0001.0008     
    mit einer Verbindung der Formel       CH.,-CH    =<B>CH</B>     -COX     umsetzt, wobei X und Y bei der Reaktion sich  abspaltende Reste bedeuten.

   Als     N-Alky        1-          arvlamine    der Formel  
EMI0001.0014     
    kommen das freie Amin bzw. seine Salze,  Metallverbindungen oder reaktionsfähigen  Derivate, und als Verbindungen der Formel       CH.,-CH    =<B>CH</B>     -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       Urisetzung    von Salzen der     Crotonsäure    mit       reaktionsfähigen    Derivaten der     N-Methyl-N-h-          toly        1-carbamiiisäure.     



  Die erhaltene neue Verbindung, das     Croton-          säure-N-inethy        1-p-toluidid,    stellt ein     schwach       gelbliches öl dar, das unter 12 mm Druck bei  153 bis 1580 siedet,     fungizid    wirkt und als  Mittel zur     Insektenvergrämung    dienen soll.  



  <I>Beispiel 1:</I>  10,5 Teile     Crotonsäureehlorid    werden unter  Rühren so zu 24,2 Teilen     N-Methyl-p-t.oluidin     getropft, dass die Temperatur auf 130 bis     1400     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  Vakuum destilliert. Das     Crotonsäure-N-me-          thyl-p-toluidid    siedet unter 12 mm Druck bei  153 bis 1580 und stellt ein schwach gelbliches  öl dar.  



  Statt in Gegenwart eines     überschusses    an       N-Methyl-p-toluidin    kann die Reaktion auch  in     (regenivart    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     Crotonsäure          wird    zusammen mit der berechneten Menge       (''lilorameiseiisäure    - N -     methyl    - 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      Erkalten nimmt man das Produkt in Äther  auf, wäscht die Lösung nacheinander mit ver  dünnter Säure, Wasser, verdünnter Lauge  und hierauf wieder mit Wasser.

   Nach Trock  nen mit Natriumsulfat wird der Äther ab  destilliert. Hierauf     wird    das als Rückstand er  haltene.     Crotonsäure    - N -     methyl    - p -     toluidid     durch Destillieren im Vakuum gereinigt. Es  siedet unter 12 mm Druck bei 153 bis 1580.



  Process for the preparation of an α, @ - 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 CH., - CH = CH = COX, where X and Y are radicals which are split off during the reaction.

   As N-Alky 1- arvlamine of the formula
EMI0001.0014
    come the free amine or its salts, metal compounds or reactive derivatives, and as compounds of the formula CH., - CH = <B> CH </B> -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 conversion of salts of crotonic acid with reactive derivatives of N-methyl-N-h-toly 1-carbamic acid.



  The new compound obtained, crotonic acid-N-methylene-1-p-toluidide, is a pale yellowish oil that boils at 153 to 1580 under 12 mm pressure, has a fungicidal effect and is intended to serve as a deterrent to insects.



  <I> Example 1: </I> 10.5 parts of crotonic acid chloride are added dropwise to 24.2 parts of N-methyl-p-t.oluidine 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 solvent that is not miscible 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 crotonic acid-N-methyl-p-toluidide boils under 12 mm pressure at 153 to 1580 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 (regenerative type of an acid-binding agent, e.g. from potash, where it is expedient to work in a solvent such as e.g. acetone .



  <I> example. 2: </I> The dry sodium salt of crotonic acid is heated together with the calculated amount ('' liloroformic acid - N - methyl - p - toluidide in a spacious flask to about 1800, until the evolution of carbon dioxide, which is strongly 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 alkali and then again with water.

   After drying with sodium sulfate, the ether is distilled off. Thereupon the residue is kept. Crotonic acid - N - methyl - p - toluidide purified by distillation in vacuo. It boils under 12 mm of pressure at 153 to 1580.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines a,ssun- gesättigten Carbonsäureamides, dadurch ge kennzeichnet, dass man ein N-Alkyl-arylamin der Formel EMI0002.0009 mit einer Verbindung der Formel <B>CH.,</B> -CH =<B>CH</B> -COX umsetzt, wobei X und Y bei der Reaktion sich abspaltende Reste bedeuten. Die erhaltene neue Verbindung, das Crotonsäure-N-methyl-p- toluidid, stellt. ein schwach gelbliches Öl dar, das unter 12 mm Druck bei<B>153</B> bis 1580 siedet. PATENT CLAIM: Process for the preparation of an α, s-unsaturated carboxamide, characterized in that an N-alkyl-arylamine of the formula EMI0002.0009 with a compound of the formula <B> CH., </B> -CH = <B> CH </B> -COX, where X and Y are radicals which are split off during the reaction. The new compound obtained, crotonic acid-N-methyl-p-toluidide, provides. is a pale yellowish oil that boils at <B> 153 </B> until 1580 under 12 mm pressure. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass ein Salz der Crotonsäure mit einem reaktionsfähigen Halogenid der N Methyl-N-p-tolyl-carbaminsäure umgesetzt wird. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that a salt of crotonic acid is reacted with a reactive halide of N methyl-N-p-tolyl-carbamic acid.
CH267563D 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide. CH267563A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH257648T 1946-06-28
CH267565T 1946-06-28
CH267563T 1946-06-28

Publications (1)

Publication Number Publication Date
CH267563A true CH267563A (en) 1950-03-31

Family

ID=27178075

Family Applications (1)

Application Number Title Priority Date Filing Date
CH267563D CH267563A (en) 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide.

Country Status (1)

Country Link
CH (1) CH267563A (en)

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