CH285691A - Process for the preparation of a quaternary ammonium compound. - Google Patents

Process for the preparation of a quaternary ammonium compound.

Info

Publication number
CH285691A
CH285691A CH285691DA CH285691A CH 285691 A CH285691 A CH 285691A CH 285691D A CH285691D A CH 285691DA CH 285691 A CH285691 A CH 285691A
Authority
CH
Switzerland
Prior art keywords
dodecanoyl
quaternary ammonium
compound
propyl
ammonium compound
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 CH285691A publication Critical patent/CH285691A/en

Links

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

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

       

  <B>Verfahren zur Herstellung einer</B>     quaternären        Ammoniumverbindung.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur Herstellung einer     quaternären          Ammoniumverbindung.    Das Verfahren ist da  durch gekennzeichnet.,     da.ss    man eine Verbin  dung der Formel  
EMI0001.0006     
    mit einer Verbindung der Formel  
EMI0001.0007     
    worin das eine X den
EMI0001.0008  
   und  das andere X Chlor bedeutet.,     umsetzt.    In Aus  führung des Verfahrens kann man     Dodeca-          noyl-N,

  N-dimethyl-aminoäthyl-N'-propyl-amid     mit     Chloracetanilid    reagieren     lassen,    oder man  setzt     1)odecanoyl-ss-chlor-äthyl-propylamid    mit       Dimethylamino-essigsäure-anilid    um.  



  Die erhaltene neue Verbindung, das     (Do-          decanoyl    -     N'-propyl    -     aminoäthyl)    -     (phenyl-car-          bamyl    -     methyl)    -     dimethyl    -     ammoniumchlorid,     zeigt einen Schmelzpunkt von 135 . Sie soll  als Desinfektionsmittel     Verwendung    finden.       Beispiel   <B><I>1.-</I></B>  <B>312</B> Teile     Dodecanoyl-N,N-dimethyl-amino-          äthyl-N'-propyl-amid    vom Siedepunkt 130 bis  150  bei 0,3 mm Druck (z.

   B. aus     Laurinsäure-          methylester    und     N,N-Dimethyl-N'-propyl-          äthylen-diamin    hergestellt) und 169,5 Teile         Chloracetanilid    werden unter Rühren 7.2 Stun  den im siedenden Wasserbad erwärmt. Die  nach dem Erkalten feste Masse wird aus       Essigester%Aceton    umkristallisiert. Man er  hält das     (Dodecanoyl-N'-propyl-aminoäthyl)-          (phenyl    -     carbamyl    -     methyl)        -dimethyl        -ammo-          niumchlorid    als weisse kristalline Substanz  vom.

   Schmelzpunkt.     7.35 ,    die klar in Wasser  löslich ist.  



  <I>Beispiel 2:</I>  304 Teile     Dodecanoyl-,B-chlor-äthyl-propyl-          amid    und<B>173</B> Teile     Dimethylamino-essigsäure-          anilid    werden in 600 Teilen     Äthylacetat    12  Stunden unter     Rückfluss    gekocht. Nach dem  Abkühlen wird das erhaltene     (Dodecanoyl-N'-          propyl    -     aminoäthyl)    -     (phenyl    -     carbamyl.    -     me-          thyl)        -dimethyl-ammoniumchlorid    abgesaugt.



  <B> Process for the production of a quaternary ammonium compound. The present patent is a process for the preparation of a quaternary ammonium compound. The process is characterized by, that one is a combination of the formula
EMI0001.0006
    with a compound of the formula
EMI0001.0007
    where one X denotes
EMI0001.0008
   and the other X is chlorine. In execution of the process one can dodecanoyl-N,

  Allow N-dimethyl-aminoethyl-N'-propyl-amide to react with chloroacetanilide, or 1) odecanoyl-ß-chloro-ethyl-propylamide is reacted with dimethylamino-acetic anilide.



  The new compound obtained, the (dodecanoyl-N'-propyl-aminoethyl) - (phenyl-carbamyl-methyl) -dimethyl-ammonium chloride, has a melting point of 135. It should be used as a disinfectant. Example <B><I>1.-</I> </B> <B> 312 </B> parts of dodecanoyl-N, N-dimethyl-amino-ethyl-N'-propyl-amide with a boiling point of 130 to 150 at 0.3 mm pressure (e.g.

   B. from lauric acid methyl ester and N, N-dimethyl-N'-propyl-ethylene-diamine) and 169.5 parts of chloroacetanilide are heated for 7.2 hours in a boiling water bath while stirring. The solid mass after cooling is recrystallized from ethyl acetate% acetone. He keeps the (dodecanoyl-N'-propyl-aminoethyl) - (phenyl-carbamyl-methyl) -dimethyl-ammonium chloride as a white crystalline substance from.

   Melting point. 7.35, which is clearly soluble in water.



  Example 2: 304 parts of dodecanoyl-, B-chloro-ethyl-propyl-amide and 173 parts of dimethylamino-acetic anilide are refluxed in 600 parts of ethyl acetate for 12 hours. After cooling, the (dodecanoyl-N'-propyl-aminoethyl) - (phenyl-carbamyl-methyl) -dimethylammonium chloride obtained is filtered off with suction.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung einer quater- närenAmmoniumverbindung, dadurch gekenn zeichnet, dass man eine Verbindung -der For mel EMI0001.0059 mit einer Verbindung der Formel EMI0001.0060 worin das eine X den EMI0001.0061 <B>und</B> das andere X Chlor bedeutet, umsetzt. PATENT CLAIM: Process for the production of a quaternary ammonium compound, characterized in that a compound of the formula EMI0001.0059 with a compound of the formula EMI0001.0060 where one X denotes EMI0001.0061 <B> and </B> the other X means chlorine, converts. Die erhaltene neue Verbindung, das (Do- decanoyl - N'-propyl - aminoäthyl) - (phenyl-car- bamyl - methyl) - dimethyl - ammoniumchlori.d, zeigt einen Schmelzpunkt von I.35 . UNTERANSPRÜCHE 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man Dodecanoyl- i'#,N-dimethyl-aminoäthyl-N'-propyl-amid mit Chloracetanilid umsetzt. The new compound obtained, the (dodecanoyl-N'-propyl-aminoethyl) - (phenyl-carbamyl-methyl) -dimethyl-ammonium chloride, has a melting point of 1.35. SUBClaims 1. The method according to claim, characterized in that dodecanoyl- i '#, N-dimethyl-aminoethyl-N'-propyl amide is reacted with chloroacetanilide. Verfahren nach Patentansprueh, da durch gekennzeichnet, dass man Dodecanoyl- ss-chlor-äthyl-propylamid mit Dimethylamino- essigsäure-anilid umsetzt. Process according to patent claim, characterized in that dodecanoyl-ss-chloro-ethyl-propylamide is reacted with dimethylamino-acetic anilide.
CH285691D 1950-02-24 1950-02-24 Process for the preparation of a quaternary ammonium compound. CH285691A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH282881T 1950-02-24
CH285691T 1950-02-24

Publications (1)

Publication Number Publication Date
CH285691A true CH285691A (en) 1952-09-15

Family

ID=25732216

Family Applications (1)

Application Number Title Priority Date Filing Date
CH285691D CH285691A (en) 1950-02-24 1950-02-24 Process for the preparation of a quaternary ammonium compound.

Country Status (1)

Country Link
CH (1) CH285691A (en)

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