CH267562A - 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
CH267562A
CH267562A CH267562DA CH267562A CH 267562 A CH267562 A CH 267562A CH 267562D A CH267562D A CH 267562DA CH 267562 A CH267562 A CH 267562A
Authority
CH
Switzerland
Prior art keywords
preparation
acid
formula
crotonic acid
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 CH267562A publication Critical patent/CH267562A/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,ss-ungesät-          tigt.en        Carbonsäureamides.    Das Verfahren ist  dadurch gekennzeichnet, dass man ein     N-Alkyl-          aryiamin    der Formel  
EMI0001.0008     
    mit einer Verbindung der Formel       CH,-CH    =     CH-COX     umsetzt, wobei X und Y bei der Reaktion sich  abspaltende Reste bedeuten.

   Als     N-Alkyl-aryl-          amine    der Formel  
EMI0001.0013     
    kommen das freie Amin bzw. seine Salze, Me  tallverbindungen oder reaktionsfähigen Deri  vate, und als Verbindungen der Formel       CH,-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-m-          tolyl-carbaminsäure.       Die erhaltene neue Verbindung, das     Cro-          tonsäure-N-äthyl-m-toluidid,    stellt ein schwach  gelbliebes öl dar, das unter 11 mm Druck bei  157 bis l60  siedet,     fungizid    wirkt und als  Mittel     zur        Insektenvergrämung    dienen soll.  



  <I>Beispiel 1:</I>  10,5 Teile     Crotonsäurechlorid    werden unter       Rübren    so zu 27 Teilen getropft, dass die Tem  peratur auf 130 bis     140     steigt. Nach dem Er  kalten wird das Reaktionsprodukt in Äther  oder einem andern mit, Wasser nicht misch  baren Lösungsmittel gelöst und die Lösung  nacheinander mit Salzsäure, Lauge und Was  ser gewaschen. Nach     Abdestillieren    des Lö  sungsmittels wird der Rückstand im Vakuum  destilliert. Das     Crotonsäure-N-äthyl-m-toluidid     siedet unter 11     rain    Druck bei 157 bis 1600 und  stellt ein     schwach    gelbliches öl dar.  



  Statt in Gegenwart eines Überschusses an       N-Äthyl-m-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     Crot.onsäure     wird zusammen mit der berechneten Menge  Chlorameisensäure - N -     ätliy    l - m -     toluidid    in  einem geräumigen Kolben auf etwa 1800 er  hitzt, bis die unter starkem Schäumen verlau  fende Kohlendioxydentwicklung beendet ist.  Man lässt auf etwa     1.000    abkühlen, setzt. heisses      Wasser     zu    und kocht kurze Zeit auf. Nach  Erkalten nimmt man das Produkt, in Äther  auf, wäscht die Lösung nacheinander     finit    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-äthyl-m-toluidid    durch  Destillieren im Vakuum gereinigt. Es siedet  unter 11 mm Druck bei 157 bis 1600.



  Process for the preparation of an α, @ - unsaturated carboxamide. The present patent relates to a process for the preparation of an a, ss-unsaturated carboxamide. The process is characterized in that an N-alkylaryiamine 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-alkyl-aryl amines of the formula
EMI0001.0013
    come the free amine or its salts, metal compounds or reactive derivatives, and as compounds of the formula CH, -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-m-tolyl-carbamic acid. The new compound obtained, the crotonic acid-N-ethyl-m-toluidide, is a pale yellow-loving oil that boils at 157 to 160 under 11 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 27 parts with stirring so that the temperature rises to 130 to 140. After he cold, 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 crotonic acid-N-ethyl-m-toluidide boils under 11 rain pressure at 157 to 1600 and is a pale yellowish oil.



  Instead of in the presence of an excess of N-ethyl-m-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.



  <I> Example 2: </I> The dry sodium salt of crotonic acid is heated together with the calculated amount of chloroformic acid - N - ätliy l - m - toluidid in a large flask to about 1800 until it fumes with strong foaming Development of carbon dioxide has ended. Allow to cool to about 1,000, set. hot water and boil for a short time. After cooling, the product is taken up in ether, the solution is washed successively with finite acid, water, dilute alkali and then again with water. After drying with sodium sulfate, the ether is distilled off.

   Thereupon the crotonic acid-N-ethyl-m-toluidide obtained as residue is purified by distillation in vacuo. It boils under 11 mm of pressure at 157 to 1600.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines a"B-un- gesättigten Carbonsäureamides, dadurch ge kennzeichnet, dass man ein N-Alkyl-arylamin der Formel EMI0002.0011 mit einer Verbindung der Formel CH,-CH = CH-C01 umsetzt, wobei \Y und Y bei der Reaktion sich abspaltende Reste bedeuten. Die erhaltene neue Verbindung, das Crotonsäure-N-äth@-1-m- t.oluidid, stellt ein schwach gelbliches Öl dar, das unter 11 mm Druck bei 157 bis 1600 siedet. PATENT CLAIM: Process for the preparation of an a "B-unsaturated carboxamide, characterized in that an N-alkyl-arylamine of the formula EMI0002.0011 with a compound of the formula CH, -CH = CH-C01, where \ Y and Y mean radicals which are split off during the reaction. The new compound obtained, crotonic acid-N-eth @ -1-m-t.oluidide, is a pale yellowish oil that boils at 157 to 1600 under 11 mm pressure. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadureh gekennzeichnet, dass ein Salz, der Crotonsäure mit einem reaktionsfähigen Halogenid der N-Äthyl-N-m-tolyl-carbaminsäure umgesetzt wird. SUBCLAIM: Method according to claim, characterized in that a salt, crotonic acid, is reacted with a reactive halide of N-ethyl-N-m-tolyl-carbamic acid.
CH267562D 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide. CH267562A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH267562T 1946-06-28
CH257648T 1946-06-28
CH267565T 1946-06-28

Publications (1)

Publication Number Publication Date
CH267562A true CH267562A (en) 1950-03-31

Family

ID=27178074

Family Applications (1)

Application Number Title Priority Date Filing Date
CH267562D CH267562A (en) 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide.

Country Status (1)

Country Link
CH (1) CH267562A (en)

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