CH267574A - 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
CH267574A
CH267574A CH267574DA CH267574A CH 267574 A CH267574 A CH 267574A CH 267574D A CH267574D A CH 267574DA CH 267574 A CH267574 A CH 267574A
Authority
CH
Switzerland
Prior art keywords
preparation
acid
formula
dichloro
ethyl
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 CH267574A publication Critical patent/CH267574A/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-nngesät-          tigten        Carbonsäureamides.    Das Verfahren ist       dadureh    gekennzeichnet, dass man ein N     Alkv1-          arylamin    der Formel  
EMI0001.0009     
    mit einer Verbindung der Formel  
EMI0001.0010     
    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  
EMI0001.0014     
    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     f,ss-Dimethyl-acryl-          säure    mit, reaktionsfähigen Derivaten der     N-          @1t.h@-1-N-3,4-dichlor-phenyl-carbaminsäure.     



  Die erhaltene neue Verbindung, das       Dimethy        lacry        lsäure-N-äthy        1-3,4@dichlor-anilid,     stellt ein schwach gelbliches Öl dar, das unter  0,05 rum Druck bei 120 bis 1260 siedet,     fun-          gizid    wirkt und als Mittel zur     Insektenvergrä-          mung    dienen soll.  



  <I>Beispiel 1:</I>  11,9 Teile     ss,ssDimethyl-acrylsäurechlorid      erden unter Rühren so zu 38 Teilen     N-Äthyl-          3,4-dichlor-anilin    getropft, dass die Tempera  tur auf 130 bis 1400 steigt. Nach dem Erkal  ten wird das     Reaktionsprodukt;    in Äther oder  einem andern mit Wasser nicht mischbaren  Lösungsmittel gelöst und die Lösung nachein  ander mit Salzsäure, Lauge und Wasser ge  waschen. Nach     Abdestillieren    des     Lösungsmit-          t        els    wird der Rückstand im Vakuum destil  liert.

   Das     Dimethylacrylsätire-N-äthyl-3,4-di-          chlor-anilid    siedet unter 0,05 mm Druck bei  120 bis 1260 und stellt ein schwach gelbliches  Öl dar.  



  Statt in Gegenwart, eines     Zrbersehusses    an       N-Äthyl-3,4-dichlor-anilin    kann die Reaktion  auch in Gegenwart eines säurebindenden Mit  tels, 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     ss,ss-Dimethyl-          acrylsäure    wird zusammen mit der berechne-           ten    Menge     Chlorameisensäure-N-äthyl-3,4-di-          chlor-anilid    in einem geräumigen Kolben auf  etwa 1800 erhitzt, bis die unter starkem Schäu  men verlaufende 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     Dimethylacrylsäiire-N-äthyl-3,4-di-          chlor-anilid    durch Destillieren im Vakuum ge  reinigt. Es siedet     unter    0,05 mm Druck bei  120 bis 1260.



  Process for the preparation of an α, @ - unsaturated carboxamide. The present patent relates to a process for the preparation of an α, l-unsaturated carboxamide. The process is characterized in that an N-alkv1-arylamine of the formula
EMI0001.0009
    with a compound of the formula
EMI0001.0010
    converts, 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
EMI0001.0014
    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 f, ss-dimethyl-acrylic acid with reactive derivatives of N- @ 1t.h @ -1-N-3,4-dichlorophenyl carbamic acid.



  The new compound obtained, dimethyl acid-N-ethy 1-3,4 @ dichloro-anilide, is a pale yellowish oil that boils under 0.05 rum pressure at 120 to 1260, has a fungicidal effect and is used as an agent to serve to deter insects.



  <I> Example 1: </I> 11.9 parts of ss, ss-dimethyl-acrylic acid chloride ground to 38 parts of N-ethyl-3,4-dichloro-aniline with stirring so that the temperature rises to 130 to 1400. After cooling th, the reaction product; dissolved in ether or another water-immiscible solvent and wash the solution one after the other with hydrochloric acid, lye and water. After the solvent has been distilled off, the residue is distilled in vacuo.

   The Dimethylacrylsätire-N-ethyl-3,4-dichloro-anilide boils under 0.05 mm pressure at 120 to 1260 and is a pale yellowish oil.



  Instead of in the presence of a Zrbersehusses of N-ethyl-3,4-dichloro-aniline, the reaction can also in the presence of an acid-binding agent, z. B. of potash, be carried out, advantageously in a solvent such. B. acetone, is worked.



  <I> Example 2: </I> The dry sodium salt of ss, ss-dimethyl-acrylic acid, together with the calculated amount of chloroformic acid-N-ethyl-3,4-dichloro-anilide, is brought to approx 1800 heated until the development of carbon dioxide, which continued under strong foaming, has ended. Allow to cool to about 1000, add hot water and boil for a short time: to. After cooling down, takes; the product is washed 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 dimethylacrylic acid-N-ethyl-3,4-dichloro-anilide obtained as residue is then purified by distillation in vacuo. It boils under 0.05 mm pressure at 120 to 1260.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines a,ss-un- gesättigten Carbonsäureamides, dadurch ge kennzeichnet, dass man ein N-Alkyl-arylamin der Formel EMI0002.0014 mit einer Verbindung der Formel EMI0002.0015 umsetzt, wobei X und Y bei der Reaktion sieh abspaltende Reste bedeuten. PATENT CLAIM: Process for the preparation of an α, β-unsaturated carboxamide, characterized in that an N-alkyl-arylamine of the formula EMI0002.0014 with a compound of the formula EMI0002.0015 converts, where X and Y in the reaction are separating radicals. Die erhaltene neue Verbindung, das Dimethy lacry lsäitre-N-äthy l- 3,4-dichlor-anilid, stellt ein schwach gelbliebes Öl dar, das unter 0,05 mm Druek bei 120 bis 1260 siedet. UNTERANSPRUCH: Verfahren nach Patentansprueh, dadurch gekennzeichnet, dass ein Salz der ss,ss-Dimethyl- acrylsäure mit einem reaktionsfähigen Halo genid der N-Äthyl-N-3,4-diehlor-phenyl-earb- aminsäure umgesetzt wird. The new compound obtained, Dimethy lacry lsäitre-N-ethy l-3,4-dichloro-anilide, is a pale yellow-loving oil that boils at 120 to 1260 below 0.05 mm pressure. SUBCLAIM: Process according to patent claim, characterized in that a salt of ss, ss-dimethyl acrylic acid is reacted with a reactive halide of N-ethyl-N-3,4-diehlor-phenyl-earbamic acid.
CH267574D 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide. CH267574A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH257648T 1946-06-28
CH267574T 1946-06-28

Publications (1)

Publication Number Publication Date
CH267574A true CH267574A (en) 1950-03-31

Family

ID=25730095

Family Applications (1)

Application Number Title Priority Date Filing Date
CH267574D CH267574A (en) 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide.

Country Status (1)

Country Link
CH (1) CH267574A (en)

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