CH267575A - 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
CH267575A
CH267575A CH267575DA CH267575A CH 267575 A CH267575 A CH 267575A CH 267575D A CH267575D A CH 267575DA CH 267575 A CH267575 A CH 267575A
Authority
CH
Switzerland
Prior art keywords
ethyl
acid
formula
preparation
dimethyl
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 CH267575A publication Critical patent/CH267575A/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,19-ungesättigten        Carhonsäureamides.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur Herstellung eines     a,ss-ungesät-          tigten        Carbonsäureamides.    Das Verfahren ist  dadurch gekennzeichnet, dass man ein     N-Allv1-          arylamin    der Formel  
EMI0001.0008     
    mit einer Verbindung der Formel  
EMI0001.0009     
         umsetzt,    wobei 1 und     5.'    bei der Reaktion     sich     abspaltende Reste bedeuten.

   Als     N-Alky        1-aryl-          amine    der Formel  
EMI0001.0016     
    kommen das freie Amin bzw. seine Salze, Me  tallverbindungen oder reaktionsfähigen Deri  vate und als Verbindungen der Formel  
EMI0001.0017     
    die freie Säure bzw. ihre reaktionsfähigen  funktionellen Derivate, wie z.

   B.     Halogenide,          Anhydride,    Ester,     Amide    oder Salze, in     Be-          traelit.    Eine spezielle Variante, die ebenfalls    nach obigem Reaktionsschema verläuft., ist die  Umsetzung von Salzen der     fl,ss-Diinethyl-acryl-          säure    mit reaktionsfähigen Derivaten der     N-          _@th@-1-N-o-anisy        1-carbaminsäure.     



  Die erhaltene neue Verbindung, das     Di-          nietliy1acrylsäure-N-äthyl-o-anisidid,    stellt, ein  schwach gelbliches Öl dar, das unter 0,2 mm       Druelz    bei<B>1.26</B> bis 1300 siedet,     fungizid    wirkt  und als Mittel zur     Insektenvergrämung    dienen  soll.  



  <I>Beispiel 1:</I>  11,9 Teile     ss,f-Dimethyl-acrylsäurechlorid          werden    unter Rühren so zu 30 Teilen     N-Äthyl-          o-anisidin    getropft, dass die Temperatur auf  130 bis     140e    steigt. Nach dem Erkalten wird  das Reaktionsprodukt in Äther oder einem  andern mit Wasser nicht mischbaren     Lösungs-          mittel    gelöst und die Lösung nacheinander mit  Salzsäure, Lauge und Wasser gewaschen. Nach       Abdestillieren    des Lösungsmittels wird der  Rückstand im Vakuum destilliert.

   Das     Di-          methylacrylsäure-N-äthyl-o-anisidid    siedet un  ter 0,2 mm Druck bei 126 bis 1300     und    stellt,  ein schwach gelbliches Öl dar.  



  Statt in     Gegenwart    eines     übersehusses    an       N-Äthyl-o-anisidin    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     fl,f'-Dimethyl-          acryisäure    wird zusammen mit der berechne-           ten    Menge     Chlorameisensäure-N-äthyl-o-anisi-          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     Dimethylacrylsäure-N-äthyl-o-anisi-          did    durch Destillieren im Vakuum gereinigt.  Es siedet unter 0,2 mm Druck bei 126 bis 130.



  Process for the preparation of an α, 19-unsaturated carboxylic acid amide. The present patent relates to a process for the preparation of an α, β-unsaturated carboxamide. The process is characterized in that an N-Allv1-arylamine of the formula
EMI0001.0008
    with a compound of the formula
EMI0001.0009
         implements, where 1 and 5. ' mean residues which split off during the reaction.

   As N-alkyl 1-aryl amines of the formula
EMI0001.0016
    come the free amine or its salts, metal compounds or reactive derivatives and as compounds of the formula
EMI0001.0017
    the free acid or its reactive functional derivatives, such as.

   B. halides, anhydrides, esters, amides or salts, in beraelite. A special variant, which also proceeds according to the above reaction scheme., Is the reaction of salts of fl, ss-diinethyl-acrylic acid with reactive derivatives of N- _ @ th @ -1-N-o-anisy 1-carbamic acid.



  The new compound obtained, the di-nietliy1acrylic acid-N-ethyl-o-anisidide, is a pale yellowish oil that boils at <B> 1.26 </B> up to 1300 under 0.2 mm pressure, has a fungicidal effect and Means to deter insects.



  Example 1: 11.9 parts of ss, f-dimethyl-acrylic acid chloride are added dropwise to 30 parts of N-ethyl-o-anisidine with stirring in such a way that the temperature rises to 130 to 140 °. 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 dimethyl acrylic acid-N-ethyl-o-anisidide boils under 0.2 mm pressure at 126 to 1300 and is a pale yellowish oil.



  Instead of in the presence of an excess of N-ethyl-o-anisidine, 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 fl, f'-dimethyl-acryic acid is heated together with the calculated amount of chloroformic acid-N-ethyl-o-aniside in a spacious flask to about 1800, until the evolution of carbon dioxide, which continues with strong 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 it. Water. After drying with sodium sulfate, the ether is distilled off. The dimethylacrylic acid-N-ethyl-o-aniside obtained as a residue is then purified by distillation in vacuo. It boils under 0.2mm pressure at 126 to 130.

Claims (1)

PATENTANSPRUCH: Verfahren mir Herstellung eines a,@-un- gesättigten Carbonsäureamides, dadurch ge kennzeichnet, dass man ein N-Alkyl-arylamin der Formel EMI0002.0018 mit einer Verbindung der Formel EMI0002.0019 umsetzt, wobei K und Y bei der Reaktion sieh abspaltende Reste bedeuten. Die erhaltene neue Verbindung, das Dimetliyi-acrylsäure-N- äthyl-o-anisidid, stellt, ein schwach gelbliches Öl dar, das unter 0,2 mm Druck bei<B>126</B> bis 1300 siedet. PATENT CLAIM: Process with the production of an a, @ - unsaturated carboxamide, characterized in that an N-alkyl-arylamine of the formula EMI0002.0018 with a compound of the formula EMI0002.0019 converts, where K and Y in the reaction are separating radicals. The new compound obtained, dimethyl-acrylic acid-N-ethyl-o-anisidide, is a pale yellowish oil that boils at 126 to 1300 under 0.2 mm pressure. UNTERANSPRUCH: Verfahren nach Patentansprueh, dadurch gekennzeichnet, dass ein Salz der f,fl-Dimetlii-l- acrylsäure mit einem reaktionsfähigen Halo genid der N-Äthyl-N-o-anisy 1-carbaminsäiire umgesetzt wird. SUBCLAIM: Process according to patent claim, characterized in that a salt of f, fl-dimethyl-1-acrylic acid is reacted with a reactive halide of N-ethyl-N-o-anisy 1-carbamic acid.
CH267575D 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide. CH267575A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH257648T 1946-06-28
CH267575T 1946-06-28

Publications (1)

Publication Number Publication Date
CH267575A true CH267575A (en) 1950-03-31

Family

ID=25730096

Family Applications (1)

Application Number Title Priority Date Filing Date
CH267575D CH267575A (en) 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide.

Country Status (1)

Country Link
CH (1) CH267575A (en)

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