CH267567A - 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
CH267567A
CH267567A CH267567DA CH267567A CH 267567 A CH267567 A CH 267567A CH 267567D A CH267567D A CH 267567DA CH 267567 A CH267567 A CH 267567A
Authority
CH
Switzerland
Prior art keywords
sep
preparation
formula
crotonic acid
methyl
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 CH267567A publication Critical patent/CH267567A/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
    • 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,@-ungesättigten        Carbonsäureamides.     
EMI0001.0003     
  
    Gegenstand <SEP> vorliegenden <SEP> Patentes <SEP> ist <SEP> ein
<tb>  \'erfaliren <SEP> zur <SEP> Herstellun <SEP> \;- <SEP> eines <SEP> u,ss-itngesät  t <SEP> i_;1 <SEP> en <SEP> (,'arl)onsä <SEP> ureaiiiides. <SEP> Das <SEP> Verfahren <SEP> ist.
<tb>  dadurch <SEP> gelzennzeieliiiet, <SEP> dass <SEP> man <SEP> einN-Alh@#l.  aiIvlamin <SEP> der <SEP> Formel     
EMI0001.0004     
         finit    einer Verbindung der Formel       CH.,---CH    -     CH-COX          mnsetzt,    wobei 1 und Y bei der Reaktion sich  abspaltende Reste bedeuten.

   Als     N-Alkyl-aryl-          ainine    der Formel  
EMI0001.0011     
    kommen das freie Amin bzw. seine Salze, Me  tallverbindungen oder reaktionsfähigen Deri  vate und als Verbindungen der Formel       CH:,        -Cfl    =     CH-CON     die freie Säure     bzw.    ihre reaktionsfähigen       funktionellen    Derivate, wie z. B.     Halogenide,          Anbydride,    Ester,     Amicle    oder Salze, in Be  tracht.

   Eine spezielle Variante, die ebenfalls  nach obigem     Reaktionssehenia    verläuft, ist die       Unisetzung    von Salzen der     Crotonsäure    mit.  reaktionsfähigen Derivaten der     N-3lethy        1-N-          p-anisy        1-earbaminsäure.       Die erhaltene neue Verbindung, das     Croton-          säure-N-methyl-p-anisidid,    stellt ein schwach  gelbliches Öl dar, das     -unter    0,1     nim    Druck bei  135 bis     7.400    siedet,

       fimgizid    wirkt und als  Mittel zur     Inselzteilvergrämung    dienen soll.  



  <I>Beispiel 1:</I>  10,5 Teile     Crotonsäureehlorid    werden Sin  ter Rühren so zu     ?7,1    Teilen     N-llethyl-p-ani-          sidin    getropft,     da.ss    die     Temperatur    auf 130  bis 1100 steigt. Nach dem     Erkalten    wird das  Reaktionsprodukt in Äther     oder    einem andern  mit     Wasser    nicht     inisehbaren        Lösungsmittel     gelöst und die Lösung nacheinander mit Salz  säure, Lauge und Wasser gewaschen.

   Nach       Abdestillieren    des     Löslni-,sniittels    wird der  Rückstand im     Vakuum    destilliert. Das     Cro-          tonsäure    - N -     metllyl    - p -     anisidid    siedet unter  0,1     inm    Druck bei 135 bis     1400    und stellt ein       selnvaeh    gelbliches Öl dar.  



  Statt in     Gegenwart    eines     Cbersehusses    an       N-Methyl-p-anisidin    kann die Reaktion     aueli     in Gegenwart eines säurebindenden Mittels,       z.    B. von     Pot.tasehe,        durehgeführt    werden, wo  bei     zweckmässig    in einem Lösungsmittel, wie  z. B. Aceton, gearbeitet. wird.  



       Beispiel        ,;?:     Das trockene     Natriumsalz    der     Crotonsäure          wird    zusammen mit der berechneten     Menge          Clilorameisensäure-N-nietliyl-p-anisidid    in       einem        geräumigen    Kolben auf etwa 1800 er  hitzt., bis die unter starkem     Seliäumen    verlau-           fende    Kohlendioxydentwicklung beendet ist.  Man lässt auf etwa 1000 abkühlen, setzt heisses       Wasser    zu und kocht kurze Zeit auf.

   Nach Er  kalten nimmt man das Produkt in Äther auf,  wäscht, die Lösung nacheinander mit verdünn  ter Säure, Wasser, verdünnter Lauge und  hierauf wieder mit Wasser. Nach Trocknen  mit Natriumsulfat wird der Äther     abdestil-          liert..    Hierauf wird das als     Riiekstand    erhal  tene     Crotonsäure-N-methyl-p-anisidid    durch  Destillieren im Vakuum gereinigt. Es siedet  unter 0,1 mm Druck bei 135 bis     1400.  



  Process for the preparation of an α, @ - unsaturated carboxamide.
EMI0001.0003
  
    The subject of <SEP> present <SEP> patent <SEP> is <SEP> a
<tb> \ 'require <SEP> for <SEP> manufacture <SEP> \; - <SEP> of a <SEP> u, ss-itngesät t <SEP> i_; 1 <SEP> en <SEP> (,' arl ) onsä <SEP> ureaiiiides. <SEP> The <SEP> procedure is <SEP>.
<tb> thereby <SEP> marked, <SEP> that <SEP> man <SEP> einN-Alh @ # l. aiIvlamin <SEP> of the <SEP> formula
EMI0001.0004
         finite with a compound of the formula CH., --- CH - CH-COX mnsetzt, where 1 and Y denote radicals splitting off during the reaction.

   As N-alkyl-aryl-ainines of the formula
EMI0001.0011
    come the free amine or its salts, metal compounds or reactive derivatives and derivatives as compounds of the formula CH :, -Cfl = CH-CON, the free acid or its reactive functional derivatives, such as. B. halides, anhydrides, esters, amicles or salts, in Be tracht.

   A special variant, which also proceeds according to the above reaction, is the dissolution of salts of crotonic acid. reactive derivatives of N-3lethy 1-N-p-anisy 1-earbamic acid. The new compound obtained, the crotonic acid-N-methyl-p-anisidide, is a pale yellowish oil that boils at 135 to 7,400 under 0.1 N under pressure,

       fimgizid acts and is intended to serve as a means to deter parts of the island.



  Example 1: 10.5 parts of crotonic acid chloride are added dropwise to 7.1 parts of N-llethyl-p-anisidine during stirring in such a way that the temperature rises to 130 to 1100. After cooling, the reaction product is dissolved in ether or another solvent that cannot be seen with water 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 crotonic acid - N - metllyl - p - anisidide boils under 0.1 m pressure at 135 to 1400 and is an almost yellowish oil.



  Instead of in the presence of an excess of N-methyl-p-anisidine, the reaction can also be carried out in the presence of an acid-binding agent, e.g. B. from Pot.tasehe, be durehführung where appropriate in a solvent such. B. acetone worked. becomes.



       Example; Allow to cool to about 1000, add hot water and boil for a short time.

   After cold, the product is taken up in ether, washed, the solution successively with dilute acid, water, dilute alkali and then again with water. After drying with sodium sulfate, the ether is distilled off. The crotonic acid-N-methyl-p-anisidide obtained as residue is then purified by distillation in vacuo. It boils under 0.1 mm pressure at 135 to 1400.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines a,ss-un- gesättigten Carbonsäureamides, dadurch ge kennzeichnet, dass man ein N-Alkyl-arylamin der Formel EMI0002.0013 mit. einer Verbindung der Formel CH, -CIi = CH -COX umsetzt, wobei X und Y bei der Reaktion sieh abspaltende Reste bedeuten. Die erhaltene neue Verbindung, das Crotonsäure-N-methyl- p-anisidid, stellt ein schwach gelbliches Öl dar, das unter 0,1 mm Druck bei 135 bis 1-100 siedet. PATENT CLAIM: A process for the preparation of an α, β-unsaturated carboxamide, characterized in that an N-alkyl-arylamine of the formula EMI0002.0013 With. a compound of the formula CH, -Cli = CH -COX, where X and Y are radicals which split off in the reaction. The new compound obtained, crotonic acid-N-methyl-p-anisidide, is a pale yellowish oil which boils at 135 to 1-100 under 0.1 mm pressure. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass ein Salz der Crotonsäure mit einem reaktionsfähigen Halogenid der N- Methyl-N-p-anisyl-carbaminsäure umgesetzt wird. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that a salt of crotonic acid is reacted with a reactive halide of N-methyl-N-p-anisyl-carbamic acid.
CH267567D 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide. CH267567A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH267567T 1946-06-28
CH257648T 1946-06-28

Publications (1)

Publication Number Publication Date
CH267567A true CH267567A (en) 1950-03-31

Family

ID=25730088

Family Applications (1)

Application Number Title Priority Date Filing Date
CH267567D CH267567A (en) 1946-06-28 1946-06-28 Process for the preparation of an α, B-unsaturated carboxamide.

Country Status (1)

Country Link
CH (1) CH267567A (en)

Similar Documents

Publication Publication Date Title
CH267567A (en) Process for the preparation of an α, B-unsaturated carboxamide.
CH267561A (en) Process for the preparation of an α, B-unsaturated carboxamide.
CH267564A (en) Process for the preparation of an α, B-unsaturated carboxamide.
CH267571A (en) Process for the preparation of an α, B-unsaturated carboxamide.
CH267572A (en) Process for the preparation of an α, B-unsaturated carboxamide.
CH267576A (en) Process for the preparation of an α, B-unsaturated carboxamide.
CH267574A (en) Process for the preparation of an α, B-unsaturated carboxamide.
CH267577A (en) Process for the preparation of an α, B-unsaturated carboxamide.
CH267568A (en) Process for the preparation of an α, B-unsaturated carboxamide.
CH267570A (en) Process for the preparation of an α, B-unsaturated carboxamide.
CH267563A (en) Process for the preparation of an α, B-unsaturated carboxamide.
CH267575A (en) Process for the preparation of an α, B-unsaturated carboxamide.
CH267578A (en) Process for the preparation of an α, B-unsaturated carboxamide.
CH267569A (en) Process for the preparation of an α, B-unsaturated carboxamide.
CH267562A (en) Process for the preparation of an α, B-unsaturated carboxamide.
CH242289A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH267579A (en) Process for the preparation of an α, B-unsaturated carboxamide.
CH311556A (en) Process for the production of a new basic substituted fatty acid amide.
CH303946A (en) Process for the preparation of a derivative of 3,5-dioxo-pyrazolidine.
CH303937A (en) Process for the preparation of a derivative of 3,5-dioxo-pyrazolidine.
CH303944A (en) Process for the preparation of a derivative of 3,5-dioxo-pyrazolidine.
CH269412A (en) Process for the representation of a basic ether.
CH238441A (en) Process for the preparation of a new diacyl derivative.
CH311572A (en) Process for the production of a new basic substituted fatty acid amide.
CH311565A (en) Process for the production of a new basic substituted fatty acid amide.