CH285689A - Process for the preparation of a quaternary ammonium compound. - Google Patents

Process for the preparation of a quaternary ammonium compound.

Info

Publication number
CH285689A
CH285689A CH285689DA CH285689A CH 285689 A CH285689 A CH 285689A CH 285689D A CH285689D A CH 285689DA CH 285689 A CH285689 A CH 285689A
Authority
CH
Switzerland
Prior art keywords
methyl
compound
dodecanoyl
quaternary ammonium
chloro
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 CH285689A publication Critical patent/CH285689A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/89—Carboxylic acid amides having nitrogen atoms of carboxamide groups quaternised
    • 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
    • A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • 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
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

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 einer     quaternären        Ammoniumverbindung.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur Herstellung einer     quaternären          Ammoniumverbindung,    dadurch     gekennzeieh-          net,    dass man eine Verbindung der Formel  
EMI0001.0007     
    mit. einer Verbindung der Formel  
EMI0001.0008     
    worin das eine X den
EMI0001.0009  
   -Rest und  das andere X Chlor bedeutet, umsetzt.

   In Aus  führung des Verfahrens kann man     Dodeca-          noyl-N,N-dinietliyl-aminoätliyl-N'-methy        1-amid     mit     Chloracet-p-ehloranilid    reagieren lassen,  oder man setzt     Dodecanoyl-ss-chlor-äthyl-ine-          thylamid    mit     Dimethyl-amino-essigsättre-p-          chlor-anilid    um.  



  Die erhaltene neue Verbindung, das (Do       deeanoyl-N'-metliyi-aininoäthyl)-(p-chlor-phe-          nylearbamyl    -     methyl)    -     dimethyl    -     ammonium-          ehlorid,    zeigt, einen Schmelzpunkt von 116 .  Sie soll als Desinfektionsmittel Verwendung  finden.  



  <I>Beispiel 1:</I>  <U>'</U>84 Teile     Dodecanoyl-N,N-dimethyl-aniino-          ät.hyl-N'-methyl-amid    vom Siedepunkt 140 bis  l60  bei 0,3 mm Druck (z. B. aus     Laurinsäure     und     Trimethyläthylendiamin    hergestellt) wer  den mit<B>1.69,5</B> Teilen     Chloracet-p-chlor-anilid     in 800 Teilen     Äthylacetat    6 Stunden unter    Rückfloss gekocht. Der beim Stehen ausgefal  lene Niederschlag wird abgesaugt.

   Nach Um  kristallisieren aus     Äthylacetat    erhält man das       (Dodecanoyl-N'-methyl-aminoäthyl)-(p-chlor-          phenyl    -     carbamyl    -     methyl)    -     dimethyl    -     ammo-          niumehlorid    als weisse Substanz vom Schmelz  punkt 116 , die klar in Nasser löslich ist.  



  <I>Beispiel 2:</I>  275,5 Teile     Doclecanoyl-ss-chlor-ä.thyl-me-          thyla.mid    und 27.3 Teile     Dimethylamino-essig-          säure-p-chlor-an.ilid    werden in 600 Teilen       Äthylacetat    12 Stunden unter Rückfloss ge  kocht.

       Naeh    dem Abkühlen wird das erhaltene       (Do(leeanoyl        -N'-metliy        l-aminoäthyl    )-     (p-chlor-          plienyl    -     earbaniyl    -     methyl    )     -climethyl    -     ammo-          niumehlorid    abgesaugt.



  Process for the preparation of a quaternary ammonium compound. The present patent relates to a process for the production of a quaternary ammonium compound, characterized in that a compound of the formula
EMI0001.0007
    With. a compound of the formula
EMI0001.0008
    in which one X denotes
EMI0001.0009
   -Rest and the other X means chlorine, converts.

   In execution of the process, dodecanoyl-N, N-dinietliyl-aminoethyl-N'-methy 1-amide can be reacted with chloroacet-p-chloroanilide, or dodecanoyl-ss-chloroethyl inethylamide is added Dimethyl-amino-acetic saturate-p-chloro-anilide.



  The new compound obtained, which (Do deeanoyl-N'-metliyi-aininoethyl) - (p-chloro-phenylearbamyl-methyl) -dimethyl-ammonium chloride, shows a melting point of 116. It should be used as a disinfectant.



  <I> Example 1: </I> <U> '</U> 84 parts of dodecanoyl-N, N-dimethyl-aniino-ethyl-N'-methyl-amide with a boiling point of 140 to 160 at 0.3 mm Pressure (e.g. made from lauric acid and trimethylethylenediamine) who refluxed with 1.69.5 parts of chloroacet-p-chloro-anilide in 800 parts of ethyl acetate for 6 hours. The precipitate which falls out on standing is filtered off with suction.

   After recrystallizing from ethyl acetate, (dodecanoyl-N'-methyl-aminoethyl) - (p-chlorophenyl - carbamyl - methyl) - dimethyl - ammonium chloride is obtained as a white substance with a melting point of 116, which is clearly soluble in water .



  Example 2: 275.5 parts of doclecanoyl-ss-chloro-ethyl-methyla.mide and 27.3 parts of dimethylamino-acetic acid-p-chloro-anilide are added in 600 parts of ethyl acetate Boiled under reflux for 12 hours.

       After cooling, the (Do (leeanoyl -N'-methyl l-aminoethyl) - (p-chloroplienyl-earbaniyl-methyl) -climethyl-ammonium chloride obtained is suctioned off.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung einer quater- nären Ammoniumverbindung, dadurch ge kennzeichnet, dass man eine Verbindung der Formel EMI0001.0057 mit. einer Verbindung der Formel EMI0001.0058 worin das eine X den EMI0001.0059 -Rest und das andere X Chlor bedeutet, umsetzt. Die erhaltene neue Verbindung, das (Dode canoyl-N'-methyl-aminoäthyl)-(p-chlor-phenyl- carbamyl-methyl)-dimethyl-ammoniumchlorid, zeigt einen Schmelzpunkt von 116 . UNTERANSPRÜCHE: 1. PATENT CLAIM: Process for the production of a quaternary ammonium compound, characterized in that a compound of the formula EMI0001.0057 With. a compound of the formula EMI0001.0058 in which one X denotes EMI0001.0059 -Rest and the other X means chlorine, converts. The new compound obtained, the (dodecanoyl-N'-methyl-aminoethyl) - (p-chlorophenyl-carbamyl-methyl) -dimethyl-ammonium chloride, has a melting point of 116. SUBCLAIMS: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man Dodecanoyl- N,N-dimethyl-aminoäthyl-N'-methyl-amid mit Chloracet-p-chlor-anilid umsetzt. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man Dodecanoyl-ss- ehlor-äthyl-methylamid mit Dimethylamino- essigsäure-p-chlor-anilid umsetzt. Process according to patent claim, characterized in that dodecanoyl-N, N-dimethyl-aminoethyl-N'-methyl-amide is reacted with chloroacet-p-chloro-anilide. 2. The method according to claim, characterized in that dodecanoyl-ss- ehlor-ethyl-methylamide is reacted with dimethylamino-acetic acid-p-chloro-anilide.
CH285689D 1950-02-24 1950-02-24 Process for the preparation of a quaternary ammonium compound. CH285689A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH282881T 1950-02-24
CH285689T 1950-02-24

Publications (1)

Publication Number Publication Date
CH285689A true CH285689A (en) 1952-09-15

Family

ID=25732214

Family Applications (1)

Application Number Title Priority Date Filing Date
CH285689D CH285689A (en) 1950-02-24 1950-02-24 Process for the preparation of a quaternary ammonium compound.

Country Status (1)

Country Link
CH (1) CH285689A (en)

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