CH267579A - 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
CH267579A
CH267579A CH267579DA CH267579A CH 267579 A CH267579 A CH 267579A CH 267579D A CH267579D A CH 267579DA CH 267579 A CH267579 A CH 267579A
Authority
CH
Switzerland
Prior art keywords
preparation
methyl
dimethyl
acid
acrylic 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 CH267579A publication Critical patent/CH267579A/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

Landscapes

  • 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,f-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-Me-          thyl-benzylamin    der Formel  
EMI0001.0008     
    mit einer Verbindung der Formel  
EMI0001.0009     
    umsetzt, wobei X und Y bei der Reaktion sich  abspaltende Reste bedeuten.  



  Die erhaltene neue Verbindung, das     Di-          methylacrylsäure-N-methyl-benzylamid,    siedet  unter 0,1 mm Druck bei 136 bis 1390 und stellt  ein gelbliches Öl dar. Es soll als Mittel zur       Insektenvergrämung    dienen.  



  <I>Beispiel 1:</I>  11,9 Teile     ss,ss-Dimethyl-acrylsäurechlorid     werden unter Rühren so zu 25 Teilen     N-Me-          thyl-benzylamin    getropft., dass die Tempera  tur 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 nachein  ander mit Salzsäure, Lauge und Wasser ge  waschen. Nach     Abdestillieren    des     Lösungsmit;          tels    wird der Rückstand im Vakuum destil  liert. Das Dimethyl-aerylsäure-N-methyl-ben-         zylamid    siedet unter 0,1 mm Druck bei 136  bis 1390 und stellt ein gelbliches Öl dar.  



  Statt in Gegenwart. eines Überschusses an       N-M        ethyl-benzylamin    kann die Reaktion auch  in Gegenwart eines säurebindenden Mittels,  z. B. von Pottasche, durchgeführt werden, wo  bei zweckmässig in einem Lösungsmittel, wie  Aceton,     gearbeitet    wird.  



  <I>Beispiel 2:</I>  Das trockene     Natriumsalz    der     ss,ss-Dimethyl-          acrylsäure    wird zusammen mit der berechne  ten Menge     Chlorameisensäure-N-methyl-ben-          zylamid    in einem geräumigen Kolben auf etwa  1800 erhitzt, bis die unter starkem Schäumen  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     Dimethylacrylsäure-N-methyl-ben-          zylamid    durch Destillieren im Vakuum gerei  nigt. Es siedet. unter 12 mm Druck bei 170  bis 1720.



  Process for the preparation of an α, f-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-methylbenzylamine of the formula
EMI0001.0008
    with a compound of the formula
EMI0001.0009
    converts, where X and Y are radicals which are split off during the reaction.



  The new compound obtained, dimethyl acrylic acid-N-methyl-benzylamide, boils under 0.1 mm pressure at 136 to 1390 and is a yellowish oil. It is intended to serve as a deterrent to insects.



  <I> Example 1: </I> 11.9 parts of SS, SS-dimethyl-acrylic acid chloride are added dropwise to 25 parts of N-methyl-benzylamine with stirring so 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 in succession with hydrochloric acid, alkali and water. After distilling off the solution; means the residue is distilled in vacuo. The dimethyl-aerylic acid-N-methyl-benzylamide boils under 0.1 mm pressure at 136 to 1390 and is a yellowish oil.



  Instead of in the present. an excess of N-M ethyl-benzylamine, the reaction can also be carried out in the presence of an acid-binding agent, e.g. B. of potash, where it is convenient to work in a solvent such as acetone.



  <I> Example 2: </I> The dry sodium salt of ss, ss-dimethyl-acrylic acid is heated together with the calculated amount of chloroformic acid-N-methyl-benzylamide in a spacious flask to about 1800 until the under strong Foaming, evolution of carbon dioxide ended. is. 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 lye and then again with water.

   After drying with sodium sulfate, the ether is distilled off. The dimethylacrylic acid-N-methyl-benzylamide obtained as residue is then purified by distillation in vacuo. It's boiling. under 12 mm pressure at 170 to 1720.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines a,fl'-un- gesät.tigten Carbonsäureamides, dadurch ge kennzeichnet, dass man ein N-Methyl-benzyl- amin der Formel EMI0002.0001 mit einer Verbindung der Formel EMI0002.0002 umsetzt, wobei X und Y bei der Reaktion sich abspaltende Reste bedeuten. Die erhaltene neue Verbindung, das Di- methylacrylsäure-N-methyl-benzylamid, siedet unter 0,1 mm Druck bei 136 bis 139 und stellt ein gelbliches Öl dar. PATENT CLAIM: Process for the preparation of an a, fl'-unsät.tierter carboxamide, characterized in that one is an N-methyl-benzylamine of the formula EMI0002.0001 with a compound of the formula EMI0002.0002 converts, where X and Y are radicals which are split off during the reaction. The new compound obtained, dimethyl acrylic acid-N-methyl-benzylamide, boils at 136 to 139 under 0.1 mm pressure and is a yellowish oil. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadureb gekennzeichnet, dass man ein Salz der ss,ss-Di- inethyl-acrylsäure mit einem reaktionsfähigen Derivat der N-1@Iethyl-N-benzyl-carbaminsäure umsetzt. SUBClaim: Process according to patent claim, characterized in that a salt of ss, ss-dimethyl-acrylic acid is reacted with a reactive derivative of N-1 @ ethyl-N-benzyl-carbamic acid.
CH267579D 1946-06-28 1946-11-16 Process for the preparation of an α, B-unsaturated carboxamide. CH267579A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH257648T 1946-06-28
CH267579T 1946-11-16

Publications (1)

Publication Number Publication Date
CH267579A true CH267579A (en) 1950-03-31

Family

ID=25730100

Family Applications (1)

Application Number Title Priority Date Filing Date
CH267579D CH267579A (en) 1946-06-28 1946-11-16 Process for the preparation of an α, B-unsaturated carboxamide.

Country Status (1)

Country Link
CH (1) CH267579A (en)

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