CH299569A

CH299569A - Process for the preparation of an ammonium compound containing trifluoromethyl groups.

Info

Publication number: CH299569A
Authority: CH
Inventors: Ag Variapat
Original assignee: Ag Variapat
Priority date: 1950-04-21
Filing date: 1950-04-21
Publication date: 1954-06-15

Description

  

  <B>Verfahren</B>     zur        Darstellung        einer        trifluormethylgruppenhaltigen        Ammoniumverbindung.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung einer     tri-          fluormethylgruppenhaltigen        Ammoniumver-          bindung,    dadurch gekennzeichnet, dass man  eine Verbindung der Formel  
EMI0001.0010     
    mit einer Verbindung der Formel  
EMI0001.0011     
    worin das eine Z den Rest  
EMI0001.0012     
    und das andere Chlor bedeutet, umsetzt.

   Man  kann beispielsweise     Dimethylaminoessigsäure-          3-trifluormethyl-4-chloranilid    mit     4-Chlor-co-          chloracetophenon    zur Reaktion bringen, oder  man setzt     Chloressigsäure-3-trifluormethyl-4-          chloranilid    mit     4-Chlor-co-dimethylaminoaceto-          phenon    um.  



  Die neue Verbindung, das     (3-Trifluor-          methyl    - 4 - chlor-     phenyl        -carbamyl-methyl)    -     (4-          chlor-phenyl-        aceto)    -     dimethyl    -     ammoniumchlo-          rid,    ein weisses Pulver vom     Schmelzpunkt       191-193 , ist in heissem Wasser löslich, hemmt  das     Bakterienwachstum    und schützt damit  behandelte Ware, wie z. B. Leinen, Wolle,  gegen das Vermorschen durch Pilze.

   Textil  materialien, Leder,     Pelzwerk,    Federn, Haare,  die dem     Angriff    von Schädlingen, wie z. B.  Mottenraupen,     Teppichkäferlarven,    ausge  setzt sind, werden durch sie vor     Beschädigung     und Zerstörung geschützt.  



       Beispiele:     1. 14 Gewichtsteile     Dimethylaminoessig-          säure-3-trifluormethyl-4-chlor-anilid        und    9,45  Gewichtsteile     4-Chlor-co-chloracetophenon    wer  den mit 60     Volumteilen    Essigester versetzt  und während einigen Stunden unter Rühren  am     Rückfluss    gekocht. Nach     einiger    Zeit be  ginnt sich das Kondensationsprodukt auszu  scheiden.

   Nach beendigter Reaktion wird  wenig     Petroläther        zugegeben,    die     quaternäre          Ammoniumverbindung        abgenutscht,    mit Essig  ester und     Petroläther    gewaschen und getrock  net.

   Man erhält so 20,5 Gewichtsteile     (3-Tri-          fluormethyl-        4-chlor-phenyl-        carbamylmethyl)      (4- chlor -     phenyl-aceto)    -     dimethyl-        amm        onium-          ehlorid    als weisses, in heissem Wasser lösliches  Pulver vom Schmelzpunkt 191-193 .  



  2. Die in Beispiel 1 beschriebene     Ammo-          niumverbindung    erhält man auch,     wenn    äqui  valente Mengen     4-Chlor-co-dimethylaminoaceto-          phenon    und     Chloracet    - 3 -     triflizormethyl    - 4     -          chloranilid    in Essigester in der oben angege  benen Weise umgesetzt werden.



  <B> Process </B> for the preparation of an ammonium compound containing trifluoromethyl groups. The present patent relates to a process for the preparation of an ammonium compound containing trifluoromethyl groups, characterized in that a compound of the formula
EMI0001.0010
    with a compound of the formula
EMI0001.0011
    where one Z is the rest
EMI0001.0012
    and the other means chlorine, converts.

   For example, dimethylaminoacetic acid 3-trifluoromethyl-4-chloroanilide can be reacted with 4-chloro-co-chloroacetophenone, or chloroacetic acid 3-trifluoromethyl-4-chloroanilide is reacted with 4-chloro-co-dimethylaminoacetophenone.



  The new compound, (3-trifluoromethyl- 4-chlorophenyl-carbamyl-methyl) - (4-chloro-phenyl-aceto) -dimethyl-ammonium chloride, a white powder with a melting point of 191-193, is in soluble in hot water, inhibits bacterial growth and protects goods treated with it, such as B. linen, wool, against rot by fungi.

   Textile materials, leather, fur, feathers, hair that can be attacked by pests such as B. caterpillars, carpet beetle larvae, are set out, are protected by them from damage and destruction.



       Examples: 1. 14 parts by weight of dimethylaminoacetic acid 3-trifluoromethyl-4-chloro-anilide and 9.45 parts by weight of 4-chloro-co-chloroacetophenone who are mixed with 60 parts by volume of ethyl acetate and refluxed for a few hours with stirring. After a while, the condensation product begins to separate out.

   After the reaction has ended, a little petroleum ether is added, the quaternary ammonium compound is suction filtered, washed with ethyl acetate and petroleum ether and net getrock.

   This gives 20.5 parts by weight of (3-trifluoromethyl-4-chloro-phenyl-carbamylmethyl) (4-chloro-phenyl-aceto) -dimethylammonium chloride as a white powder which is soluble in hot water and has a melting point of 191- 193.



  2. The ammonium compound described in Example 1 is also obtained if equivalent amounts of 4-chloro-co-dimethylaminoacetophenone and chloroacet-3-triflizormethyl-4-chloroanilide are reacted in ethyl acetate in the manner indicated above.

Claims

PATENT CLAIM Process for the preparation of an ammonium compound containing trifluoromethyl groups, characterized in that a compound of the formula EMI0002.0006 with a compound of the formula EMI0002.0008 where one Z is the rest EMI0002.0009 and the other means chlorine, converts.

The new compound, the (3-trifluoromethyl-4-chlorophenyl-carbamyl-methyl) - (4-chlorophenyl-aceto) -dimethylammonium chloride, a white powder with a melting point of 191-193, is soluble in hot water and inhibits the bacteria rien growth and protects goods treated with it, such as B. linen, wool, against rot by fungi. Textile materials, leather, fur, feathers, hair that attacked by pests such. B. caterpillars, carpet beetle larvae are exposed, are protected from damage and destruction by them.

SUB-CLAIMS: 1. Process according to claim, characterized in that dimet.hylaminoacetic acid-3-trifluoromethyl-4-chloroanilide is reacted with 4-chloro-w-chloroacetophenone. 2. The method according to claim, characterized in that 4-chloro-co-dimethylaminoacetophenone is reacted with chloroacet-3-trifluoromethyl-4-chloroanilide.