CH210475A - Process for the preparation of a quaternary aminoacetic acid amide derivative. - Google Patents

Process for the preparation of a quaternary aminoacetic acid amide derivative.

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Publication number
CH210475A
CH210475A CH210475DA CH210475A CH 210475 A CH210475 A CH 210475A CH 210475D A CH210475D A CH 210475DA CH 210475 A CH210475 A CH 210475A
Authority
CH
Switzerland
Prior art keywords
quaternary
preparation
acid amide
amide derivative
dichloroanilide
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 CH210475A publication Critical patent/CH210475A/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 Darstellung eines     quaternären        Aminoessigsäureamidderivates.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Darstellung eines     quater-          nären        Aminoessigsäureamidderivates,    dadurch  gekennzeichnet, dass man     Chloressigsäure-          3,4-dichloranilid    mit     Dimethylamin    umsetzt    und das erhaltene     Dimethylaminoessigsäure-          3,4-dichloranilid    mit     3,

  4-Dichlor-co-ohloraceto-          phenon    in die     quaternäre    Verbindung der  wahrscheinlichen Formel  
EMI0001.0014     
    überführt. Die neue Verbindung, ein weisses  Pulver, ist in Wasser klar löslich und eignet  sich zum Schützen von Pelzwerk, Federn,  Haaren, Leder,     fibrösen    Materialien und der  gleichen vor Mottenraupen und andern Frass  schädlingen und als     fungicides    und     bacteri-          cides    Mittel.         Beispiel:     162 Teile     3,4-Dichloranilin    werden in  500 Teilen Benzol gelöst und bei<B>500</B> unter  Rühren mit 135 Teilen     Chloracetylchlorid     versetzt.

   Es fällt ein dicker Brei aus, der  sich allmählich unter     HCI-Entwicklung    löst.    Nach 12stündigem Rühren bei<B>50'</B> wird  noch eine Stunde zum Sieden erhitzt, filtriert  und nach dem Erkalten das     Chloressigsäure-          3,4-dichloranilid    abgesaugt und getrocknet.  



  23,8 Teile dieser Verbindung werden bei  Zimmertemperatur in 55 Teile     20 /oige        Di-          methylaminlösung    eingerührt und das Ganze  nach einer Stunde auf     5011    aufgeheizt. Die  Reaktion ist beendet, wenn eine Probe der       inhomogenen        Mischung    in verdünnter Salz  säure klar löslich ist. Nach dem Abkühlen  wird das sich in eine halbfeste und eine       wässrige    Schicht scheidende Reaktionsgemisch  getrennt und die nicht     wässrige    Schicht mit      Wasser gewaschen. Sie erstarrt meist spontan  oder aber nach dem     Animpfen.     



  24,7 Teile     Dimethylanrinoessigsärrr-e-3,4-          dichloranilid    und<B>25</B> Teile     3,4-Diehlor-co-          chloracetophenon    werden in 200 Teilen     Toluol     über Nacht gekocht. Es fällt ein weisses  Pulver aus, welches abgesaugt, mit     Toluol     gewaschen und im     Vakuum    getrocknet wird.



  Process for the preparation of a quaternary aminoacetic acid amide derivative. The subject matter of the present patent is a process for the preparation of a quaternary aminoacetic acid amide derivative, characterized in that chloroacetic acid-3,4-dichloroanilide is reacted with dimethylamine and the dimethylaminoacetic acid-3,4-dichloroanilide obtained with 3,

  4-dichloro-co-chloroacetophenone into the quaternary compound of the probable formula
EMI0001.0014
    convicted. The new compound, a white powder, is clearly soluble in water and is suitable for protecting fur, feathers, hair, leather, fibrous materials and the like from pests of moths and other feeding stuff and as a fungicidal and bactericidal agent. Example: 162 parts of 3,4-dichloroaniline are dissolved in 500 parts of benzene and, at <B> 500 </B>, 135 parts of chloroacetyl chloride are added while stirring.

   A thick pulp falls out, which gradually dissolves with the development of HCI. After stirring for 12 hours at 50 ', the mixture is heated to boiling for a further hour, filtered and, after cooling, the 3,4-dichloroacetic acid-3,4-dichloroanilide is filtered off with suction and dried.



  23.8 parts of this compound are stirred into 55 parts of 20% dimethylamine solution at room temperature and the whole is heated to 5011 after one hour. The reaction is over when a sample of the inhomogeneous mixture is clearly soluble in dilute hydrochloric acid. After cooling, the reaction mixture, which separates into a semi-solid and an aqueous layer, is separated and the non-aqueous layer is washed with water. It usually solidifies spontaneously or after inoculation.



  24.7 parts of dimethylanrinoacetic acid-3,4-dichloroanilide and 25 parts of 3,4-diehlor-co-chloroacetophenone are boiled in 200 parts of toluene overnight. A white powder precipitates out, which is filtered off with suction, washed with toluene and dried in vacuo.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines quater- nären Aminoessigsäurea,midderivates, dadurch gekennzeichnet, dass man Chloressigsäure- 3,4-dichloranilid mit Dimethylamin umsetzt und das erhaltene Dimethylamirroessigsärrre- 3,4-dichloranilid mit 3,4-Dichlor-co-chloraceto- phenon in die quaternäre Verbindung über führt. PATENT CLAIM: Process for the preparation of a quaternary Aminoessigsäurea, midderivates, characterized in that one reacts chloroacetic acid-3,4-dichloroanilide with dimethylamine and the resulting dimethylamirroacetic acid 3,4-dichloroanilide with 3,4-dichloro-co-chloroacetophenone leads into the quaternary connection. Die neue Verbindung, ein weisses Pulver, ist in Wasser klar löslich und eignet sich zum Schützen von Pelzwerk, Federn, Haaren, Leder, fibrösen Materialien und der gleichen vor Mottenraupen und andern Frass schädlingen und als fungicides und bacteri- cides Mittel. The new compound, a white powder, is clearly soluble in water and is suitable for protecting fur, feathers, hair, leather, fibrous materials and the like from pests of moths and other feeding stuff and as a fungicidal and bactericidal agent.
CH210475D 1935-12-23 1938-07-11 Process for the preparation of a quaternary aminoacetic acid amide derivative. CH210475A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE198052X 1935-12-23
CH210475T 1938-07-11

Publications (1)

Publication Number Publication Date
CH210475A true CH210475A (en) 1940-07-15

Family

ID=25724889

Family Applications (1)

Application Number Title Priority Date Filing Date
CH210475D CH210475A (en) 1935-12-23 1938-07-11 Process for the preparation of a quaternary aminoacetic acid amide derivative.

Country Status (1)

Country Link
CH (1) CH210475A (en)

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