CH267568A - 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
CH267568A
CH267568A CH267568DA CH267568A CH 267568 A CH267568 A CH 267568A CH 267568D A CH267568D A CH 267568DA CH 267568 A CH267568 A CH 267568A
Authority
CH
Switzerland
Prior art keywords
preparation
acid
methyl
formula
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 CH267568A publication Critical patent/CH267568A/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     cc,@-ungesättigten        Carbonsäureamides.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur Herstellung eines     a,f-tuigesät-          tigten        Carbonsäureamides.    Das Verfahren ist  dadurch gekennzeichnet,     dass    man ein     N-Alkyl-          arylamin    der Formel  
EMI0001.0009     
    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     A1kyl-ary-l.-          amine    der Formel  
EMI0001.0015     
    kommen das freie Amin bzw. seine Salze, Me  tallverbindungen oder     reaktionsfähigen    Deri  vate und als     Verbindungen    der Formel  CH     f-CI4    =     CH        -COX     die freie Säure bzw. ihre reaktionsfähigen  funktionellen Derivate, wie z. B.     Halogenide,          Anhydride,    Ester,     Ainide    oder Salze, in Be  tracht.

   Eine spezielle Variante, die ebenfalls  nach obigem Reaktionsschema verläuft, ist die  Unisetzung von Salzen der     Crotonsäure    mit    reaktionsfähigen Derivaten der     N-Methyl-N-          3,4-dimethy        1-phenyl-carbaminsäure.     



  Die erhaltene neue Verbindung, das     Cro-          tonsätire-N-metliyl-3,4-dimethyl-anilid,    stellt  ein schwach gelbliches Öl dar, das unter  0,6 mm Druck bei 136 bis 1390 siedet,     fungizid     wirkt und als Mittel zur     Insektenvergrämung     dienen soll.  



  <I>Beispiel 1:</I>  10,5 Teile     Crotonsäurechlorid    werden unter  Rühren so zu 27 Teilen     N-Methyl-3,4-dimethyl-          anilin    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 nacheinander mit Salz  säure, Lauge und Wasser gewaschen. Nach       Abdestillieren    des Lösungsmittels wird der  Rückstand im     Vakuum    destilliert. Das     Croton-          säure-N-inethyl-3,4-dimethylanilid    siedet unter  0,6 mm Druck bei 136 bis 1390 und stellt ein  schwach gelbliches Öl dar.  



  Statt in Gegenwart eines Überschusses an       N-3,4-Trimethyl-anilin    kann die Reaktion auch  in Gegenwart 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     -Ienge              Chlorameisensäure-N-Alethyl-3,4-dimethyl-ani-          lid    in einem geräumigen Kolben auf etwa 1800  erhitzt, bis die unter starkem Schäumen ver  laufende     Kohlendioxydentwicklung    beendet  ist. Man lässt auf etwa<B>1000</B>     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     Crotonsäure-N-methyl-3,4-dimethyl-          anilid    durch Destillieren im Vakuum     gerei-          Illgt.    Es siedet unter 0,6 mm Druck bei 136 bis  1390.



  Process for the preparation of a cc, @ - unsaturated carboxamide. The subject of the present patent is a process for the preparation of an α, f-tuigesät- saturated carboxamide. The process is characterized in that an N-alkylarylamine of the formula
EMI0001.0009
    with a compound of the formula CH, -CH = <B> CH </B> -COX, where X and Y are radicals which are split off during the reaction.

   As N-alkyl-ary-l-amines of the formula
EMI0001.0015
    come the free amine or its salts, metal compounds or reactive derivatives and as compounds of the formula CH f-Cl4 = 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 conversion of salts of crotonic acid with reactive derivatives of N-methyl-N-3,4-dimethyl-1-phenyl-carbamic acid.



  The new compound obtained, the Crotonsätire-N-methyl-3,4-dimethyl-anilide, is a pale yellowish oil that boils at 136 to 1390 under 0.6 mm pressure, has a fungicidal effect and serves as an agent to deter insects should.



  Example 1: 10.5 parts of crotonic acid chloride are added dropwise to 27 parts of N-methyl-3,4-dimethylaniline 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 successively with hydrochloric acid, alkali and water. After the solvent has been distilled off, the residue is distilled in vacuo. Crotonic acid N-ynethyl-3,4-dimethylanilide boils under 0.6 mm pressure at 136 to 1390 and is a pale yellowish oil.



  Instead of in the presence of an excess of N-3,4-trimethyl-aniline, the reaction can also be carried out in the presence of an acid-binding agent, e.g. B. of potash, where appropriate in a solvent, such as. 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-Alethyl-3,4-dimethyl-anilide in a large flask to about 1800 until the under strong Foaming ver ongoing evolution of carbon dioxide has ended. Allow to cool to about <B> 1000 </B>, 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 crotonic acid-N-methyl-3,4-dimethylanilide obtained as residue is then purified by distillation in vacuo. It boils under 0.6 mm pressure at 136 to 1390.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines a,ss-unge- sättigten Carbonsäureamides, dadurch gekenn zeichnet, dass man ein N-Alkyl-arylamin der Formel EMI0002.0019 mit einer Verbindung der Formel CH, -CH =<B>CH</B> -COX umsetzt, wobei X und F bei der Reaktion sieh abspaltende Reste bedeuten. Die erhaltene neue Verbindung, das Crotonsäure-N-methy l- 3,4-dimethyl-anilid, stellt. ein schwach gelb liches Öl dar, das unter 0,6 mm Druck bei 136 bis 1390 siedet. PATENT CLAIM: A process for the preparation of an a, ß-unsaturated carboxamide, characterized in that an N-alkyl-arylamine of the formula EMI0002.0019 with a compound of the formula CH, -CH = <B> CH </B> -COX, where X and F are radicals which split off in the reaction. The new compound obtained, the crotonic acid-N-methyl-3,4-dimethyl-anilide, is. is a pale yellowish oil that boils at 136 to 1390 under 0.6 mm pressure. UNTERANSPRUCH Verfahren nach Patentanspruch, dadurch gekennzeichnet:, dass ein Salz der Crotonsäure mit einem reaktionsfähigen Halogenid von N- Methyl-N- 3,4-dimethyl-pheny 1-earbaminsäure umgesetzt wird. SUBCLAIM Process according to claim, characterized in that a salt of crotonic acid is reacted with a reactive halide of N-methyl-N-3,4-dimethyl-pheny 1-earbamic acid.
CH267568D 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide. CH267568A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH257648T 1946-06-28
CH267568T 1946-06-28

Publications (1)

Publication Number Publication Date
CH267568A true CH267568A (en) 1950-03-31

Family

ID=25730089

Family Applications (1)

Application Number Title Priority Date Filing Date
CH267568D CH267568A (en) 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide.

Country Status (1)

Country Link
CH (1) CH267568A (en)

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