CH267580A - 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
CH267580A
CH267580A CH267580DA CH267580A CH 267580 A CH267580 A CH 267580A CH 267580D A CH267580D A CH 267580DA CH 267580 A CH267580 A CH 267580A
Authority
CH
Switzerland
Prior art keywords
preparation
dimethyl
acrylic acid
unsaturated carboxamide
formula
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 CH267580A publication Critical patent/CH267580A/en

Links

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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/08—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
    • 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

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)

Description

       

  Verfahren zur Herstellung eines     cz,ss-ungesättigten        Carbonsäureamides.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur Herstellung eines     a,ss-ungesät-          tigten        Carbonsäureamides.    Das Verfahren ist  dadurch gekennzeichnet, dass man ein sekun  däres, kondensiert aromatisches,     heterocycli-          sehes    Amin 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     ss,ss-Di-          methyl-acrylsäure-tetrahydro-eliinolid,    siedet  unter 0,1 mm Druck bei 139 bis 1430. Es soll  als Mittel zur     Insektenvergrämung    dienen.  



  <I>Beispiel:</I>  Das trockene     Natriumsalz    der     ss,ss-Di-          methyl-acrylsäure        wird        zusammen        mit        90%     der äquivalenten Menge an Chlorameisen  säure-tetrahydrocliinolid (hergestellt aus     Te-          trahydrochinolin    durch Einleiten von     Phosgen     bei 20 bis 500) in einem geräumigen Kolben  bis zur Beendigung der Reaktion auf<B>175</B> bis  1800 erhitzt. Hierauf lässt man abkühlen, ver  setzt das Reaktionsgemisch mit     Xylol    und  wäscht. mit verdünnter Salzsäure, verdünnter    Natronlauge und Wasser.

   Nach dem     Abdestil-          lieren    des     Xylols    wird das zurückbleibende     ss,ss-          Dimethyl-acrylsäure-tetrahydro-chinolid    im  Vakuum destilliert. Es siedet bei 139 bis 1430  unter 0,1 mm Druck.



  Process for the preparation of a cz, ss-unsaturated carboxamide. The present patent relates to a process for the preparation of an α, β-unsaturated carboxamide. The process is characterized in that a secondary, condensed aromatic, heterocyclic amine of the formula is used
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, the ss, ss-dimethyl-acrylic acid-tetrahydro-eliinolide, boils under 0.1 mm pressure at 139 to 1430. It is said to serve as a means to deter insects.



  <I> Example: </I> The dry sodium salt of ss, ss-dimethyl-acrylic acid is used together with 90% of the equivalent amount of chloroformic acid tetrahydrocliinolide (made from tetrahydroquinoline by introducing phosgene at 20 to 500) Heated to <B> 175 </B> to 1800 in a large flask until the reaction is complete. It is then allowed to cool, the reaction mixture is added with xylene and washed. with dilute hydrochloric acid, dilute sodium hydroxide solution and water.

   After the xylene has been distilled off, the ss, ss-dimethyl-acrylic acid-tetrahydroquinolide that remains is distilled in vacuo. It boils at 139 to 1430 under 0.1 mm pressure.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines a,ss-un- gesättigten Carbonsäureamides, dadurch ge kennzeichnet, dass man ein sekundäres, kon densiert aromatisches, heterocy clisches Amin der Formel EMI0001.0034 mit einer Verbindung der Formel EMI0001.0035 umsetzt, wobei X und Y bei der Reaktion sich abspaltende Reste bedeuten. Die erhaltene neue Verbindung, das ss,ss- Dimethyl-acrylsäure-t.etrahydro-chinolid, sie det unter 0,1 mm Druck bei 139 bis 1430. PATENT CLAIM: Process for the preparation of an a, ß-unsaturated carboxamide, characterized in that a secondary, condensed aromatic, heterocyclic amine of the formula EMI0001.0034 with a compound of the formula EMI0001.0035 converts, where X and Y are radicals which are split off during the reaction. The new compound obtained, the ss, ss-dimethyl-acrylic acid-t.etrahydroquinolide, it det under 0.1 mm pressure at 139 to 1430. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man ein Salz der ss,ss-Di- inethyl-acrylsäure mit einem reaktionsfähigen Derivat des N-Carboxy-tetrahydrochinolins umsetzt. SUBSTITUTE SHEET: Process according to patent claim, characterized in that a salt of ss, ss-dimethyl-acrylic acid is reacted with a reactive derivative of N-carboxy-tetrahydroquinoline.
CH267580D 1946-06-28 1946-11-16 Process for the preparation of an α, B-unsaturated carboxamide. CH267580A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH257648T 1946-06-28
CH267580T 1946-11-16

Publications (1)

Publication Number Publication Date
CH267580A true CH267580A (en) 1950-03-31

Family

ID=25730101

Family Applications (1)

Application Number Title Priority Date Filing Date
CH267580D CH267580A (en) 1946-06-28 1946-11-16 Process for the preparation of an α, B-unsaturated carboxamide.

Country Status (1)

Country Link
CH (1) CH267580A (en)

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