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CH206897A - Process for the preparation of a quaternary amino fatty acid amide derivative. - Google Patents

Process for the preparation of a quaternary amino fatty acid amide derivative.

Info

Publication number
CH206897A
CH206897A CH206897DA CH206897A CH 206897 A CH206897 A CH 206897A CH 206897D A CH206897D A CH 206897DA CH 206897 A CH206897 A CH 206897A
Authority
CH
Switzerland
Prior art keywords
fatty acid
amide derivative
acid amide
preparation
quaternary amino
Prior art date
Application number
Other languages
German (de)
Inventor
A-G J R Geigy
Original Assignee
Geigy Ag J R
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 Geigy Ag J R filed Critical Geigy Ag J R
Publication of CH206897A publication Critical patent/CH206897A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • 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
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung eines     quaternären        Aminofettsäureamidderivates.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur     I3erstellung    eines     quater-          nä.ren        Aminofettsäureamidderivates,    dadurch  gekennzeichnet, dass man a -     Chlorpropion-          säure-4-(4'-chlorphenoxy)-anilid,    darstellbar  aus 4 -     Amino    - 4'-     chlordiphenyläther    und     a-          Chlorpropionylchlorid,

      mit     Dimethylamin     umsetzt und das erhaltene     a-Dimethylamino-          propionsäure-4-(4'-chlorphenoxy)-anilid    mit       2-Chlorbenzylchlorid    in die     quaternäre    Ver  bindung überführt.  



  Die neue Verbindung,     ein        weisses,        in    Was  ser lösliches Pulver, eignet sich zum     Schützen     von Pelzwerk, Federn,     Haaren,    Leder,     fibrö-          sen    Materialien und dergleichen vor Motten  raupen und andern     Frassschädlingen    und als       fungicides    und     bactericides    Mittel.  



       Beispiel:     Zu 90 Teilen wässriger     Dimethylamin-          lösung    von<B>19 ,wo</B> werden<B>300</B> Volumenteile  Alkohol und 43 Teile a-Chlorpropionsäure-4-         (4'-chlorphenoxy)-anilid,    hergestellt aus 4  Amino-4'-chlordiphenyläther und     a-Chlorpro-          pionylchlorid,    zugesetzt und die Mischung  während 20     Stunden    bei 40 bis<B>50'</B> C ge  rührt. Aus der erhaltenen Lösung     werden    der  Alkohol und das     überschüssige        Dimethylamin     mit Wasserdampf abgeblasen.

   Das ölige     a-          Dimethylamino    -     propionsäure    - 4 - (4' - chlor  phenoxy)-anilid wird mit Äther aufgenom  men, getrocknet und nach dem     Abdestillieren     des     Extraktionsmittels    als festes, in verdünn  ter Salzsäure leicht lösliches Produkt gewon  nen.  



  6 Teile     a-Dimethylaminopropionsäure-4-          (4'-chlorphenoxy)-anüid    werden     in    50 Volu  menteilen Benzol gelöst und mit 5     Teilen        2-          Chlorbenzylchlorid    während 24     Stunden    auf  70 bis<B>80'</B> C erwärmt. Nach dem Abkühlen  erhält man 7 Teile der farblosen kristallini  schen     quaternären    Verbindung. Nach dem       Abfiltrieren    und Trocknen     bildet    die neue  Verbindung ein weisses,     in    Wasser lösliches       Pulver.  



  Process for the preparation of a quaternary amino fatty acid amide derivative. The subject matter of the present patent is a process for the production of a quaternary amino fatty acid amide derivative, characterized in that a - chloropropionic acid 4- (4'-chlorophenoxy) anilide, which can be prepared from 4 - amino - 4'-chlorodiphenyl ether and a- chloropropionyl chloride,

      reacted with dimethylamine and the α-dimethylaminopropionic acid 4- (4'-chlorophenoxy) anilide obtained was converted into the quaternary compound with 2-chlorobenzyl chloride.



  The new compound, a white powder that is soluble in water, is suitable for protecting fur, feathers, hair, leather, fibrous materials and the like from caterpillars and other feeding pests and as a fungicidal and bactericidal agent.



       Example: To 90 parts of aqueous dimethylamine solution of <B> 19, where <B> 300 </B> parts by volume of alcohol and 43 parts of α-chloropropionic acid-4- (4'-chlorophenoxy) -anilide are produced from 4 amino-4'-chlorodiphenyl ethers and α-chloropropionyl chloride, added and the mixture stirred at 40 to 50 ° C for 20 hours. The alcohol and the excess dimethylamine are blown off with steam from the solution obtained.

   The oily α-dimethylamino propionic acid 4 - (4 '- chlorophenoxy) anilide is taken up with ether, dried and, after the extraction agent has been distilled off, won as a solid product that is easily soluble in dilute hydrochloric acid.



  6 parts of a-dimethylaminopropionic acid-4- (4'-chlorophenoxy) anuide are dissolved in 50 parts by volume of benzene and heated with 5 parts of 2-chlorobenzyl chloride to 70 to 80 ° C for 24 hours. After cooling, 7 parts of the colorless crystalline quaternary compound are obtained. After filtering off and drying, the new compound forms a white powder that is soluble in water.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines quater- nären Aminofettsäureamidderivates, dadurch gekennzeichnet, dass man a-Chlorpropion- säure-4-(4'-chlorphenogy)-anilid mit Dime- thylamin umsetzt und das erhaltene a-Dime- thylaminopropionsäure-4,- (4'-chlorphenogy) PATENT CLAIM: Process for the production of a quaternary amino fatty acid amide derivative, characterized in that a-chloropropionic acid-4- (4'-chlorophenogy) -anilide is reacted with dimethylamine and the a-dimethylaminopropionic acid-4, - ( 4'-chlorphenogy) - anilid mit 2-Chlorbenzylchlorid in die quater- näre Verbindung überführt. Die neue Verbindung, ein weisses, in Was ser lösliches Pulver, eignet sich zum Schüt zen von Pelzwerk, Federn, Haaren, Leder, fibrösen Materialien und dergleichen vor Mot tenraupen und andern Frassschädlingen und als fungicides und bactericides Mittel. - anilide is converted into the quaternary compound with 2-chlorobenzyl chloride. The new compound, a white powder that is soluble in water, is suitable for protecting fur, feathers, hair, leather, fibrous materials and the like against caterpillars and other feeding pests and as a fungicidal and bactericidal agent.
CH206897D 1935-12-23 1938-02-04 Process for the preparation of a quaternary amino fatty acid amide derivative. CH206897A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE198052X 1935-12-23
DE206897X 1937-02-05

Publications (1)

Publication Number Publication Date
CH206897A true CH206897A (en) 1939-08-31

Family

ID=25758405

Family Applications (1)

Application Number Title Priority Date Filing Date
CH206897D CH206897A (en) 1935-12-23 1938-02-04 Process for the preparation of a quaternary amino fatty acid amide derivative.

Country Status (1)

Country Link
CH (1) CH206897A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2441498A (en) * 1943-07-15 1948-05-11 Astra Apotekarnes Kem Fab Alkyl glycinanilides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2441498A (en) * 1943-07-15 1948-05-11 Astra Apotekarnes Kem Fab Alkyl glycinanilides

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