CH299567A

CH299567A - Process for the preparation of an ammonium compound containing trifluoromethyl groups.

Info

Publication number: CH299567A
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

  

  Verfahren     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  
EMI0001.0009     
    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     3,4-Dichlor-          benzylchlorid    zur Reaktion     bringen,    oder man  setzt     3,4-Diehlorbenzyl-dimethyl-amin    mit       Chloressigsäure-3-trifluormethyl-4-chloranilid     um.  



  Das     neueVerbindung,    das (4-.Chlor-3-trifluor       methylphenyl-carbamyl-methyl)-(3,4-dichlor-          benzyl)-dimethylammoniumchlorid,    ein weisses    Pulver vom Schmelzpunkt 190-191 ,     .ist    in  heissem Wasser löslich, hemmt das Bakterien  wachstum und schützt     damitSehandelte    Ware,       wie    z: B. Leinen, Wolle, gegen das Vermor  schen durch Pilze. Textilmaterialien, Leder,  Pelzwerk, Federn, Haare, die dem Angriff  von     Schädlingen,    wie z. B.

   Mottenraupen,       Teppichkäferlarven,        _        ausgesetzt    sind, werden  durch sie vor Beschädigung und     Zerstörung     geschützt.  



  <I>Beispiele:</I>  1. 14     Gewichtsteile        Dimethylaminoessig-          säure-3-trifluormethyl-4-chloranilid    und 20       Gewichtsteile        3,4-Dichlorbenzyl-ehlorid    werden  in 100     Volumteilen    Essigester gelöst und das  Ganze 12 Stunden auf dem Wasserbad unter       Rückfluss    gerührt. Nach einiger Zeit beginnt  sich das     Kondensationsprodukt    auszuscheiden.

    Nach     beendigter    Reaktion wird die     quaternäre          Ammoniumverbindung        abgenutscht,    mit Essig  ester und     Petroläther        gewaschen    und getrock  net. Man erhält so 30 Gewichtsteile     (4-Chlor-          3-trifluormethylphenyl-carbamyl-methyl)-    (3,4  dichlorbenzyl)-dimethylammoniumchlorid, das  ein weisses, in heissem Wasser lösliches Pulver  vom Schmelzpunkt<B>190-1910</B> darstellt.  



  2. Zu der in     \,Beispiel    1 beschriebenen,       quaternären        Verbindung        gelangt    man auch,  wenn äquivalente Mengen     3,4-Dichlor-benzyl-          dimethylamin    und     Chloressigsäure-3-trifluor-          4-chloranilid    in     Essigester    nach der oben an  gegebenen Weise umgesetzt werden.



  Process for the preparation of an ammonium compound containing trifluoromethyl groups. The subject of the present patent is a process for the production of an ammonium compound containing trifluoromethyl groups, characterized in that a compound is used. the formula
EMI0001.0009
    with a compound of the formula
EMI0001.0011
    where one Z is the rest
EMI0001.0012
    and the other means chlorine,

       implements. For example, dimethylaminoacetic acid 3-trifluoromethyl-4-chloroanilide can be reacted with 3,4-dichlorobenzyl chloride, or 3,4-dichlorobenzyl-dimethylamine is reacted with chloroacetic acid 3-trifluoromethyl-4-chloroanilide.



  The new compound, (4-chloro-3-trifluoro methylphenyl-carbamyl-methyl) - (3,4-dichlorobenzyl) -dimethylammonium chloride, a white powder with a melting point of 190-191, is soluble in hot water and inhibits this Bacteria grow and thus protect the traded goods, such as linen, wool, against spoilage caused by fungi. Textile materials, leather, fur, feathers, hair that are prone to attack by pests such as B.

   Moth caterpillars, carpet beetle larvae, _ are exposed, are protected from damage and destruction by them.



  <I> Examples: </I> 1. 14 parts by weight of dimethylaminoacetic acid 3-trifluoromethyl-4-chloroanilide and 20 parts by weight of 3,4-dichlorobenzyl chloride are dissolved in 100 parts by volume of ethyl acetate and refluxed for 12 hours on a water bath touched. After a while the condensation product begins to separate out.

    After the reaction has ended, the quaternary ammonium compound is filtered off with suction, washed with ethyl acetate and petroleum ether and net getrock. This gives 30 parts by weight of (4-chloro-3-trifluoromethylphenyl-carbamyl-methyl) - (3,4 dichlorobenzyl) -dimethylammonium chloride, which is a white powder which is soluble in hot water and has a melting point of 190-1910 .



  2. The quaternary compound described in Example 1 can also be obtained when equivalent amounts of 3,4-dichlorobenzyldimethylamine and 3-trifluoro-4-chloroacetic acid are reacted in ethyl acetate in the manner given above.

Claims

PATENT CLAIM: Process for the production of an ammonite compound containing trifluoromethyl groups, characterized in that a compound of the formula EMI0002.0006 io with a compound of the formula EMI0002.0008 1s where one Z is the rest EMI0002.0009 20 and the other means chlorine, converts.

The new compound, the (4-chloro-3-trifluoromethylphenyl-carbamyl-methyl) - (3,4-dichlorobenzyl) -dimethylammonium chloride, a white powder with a melting point of 190-191, is soluble in hot water, inhibits bacteria growth and protects treated goods, such as B. Linen, wool, against spoilage by fungi. Textile materials, leather. Furs, feathers, hair that are prone to attack by pests such as B. caterpillars, carpet beetle larvae are exposed, are protected from damage and destruction by them.

SUBClaims: 1. Process according to patent claim, characterized in that dimethylaminoacetic acid 3-trifluoromethyl-4-chloroanilide is reacted with 3,4-dichlorobenzyl chloride. 2. The method according to claim, characterized in that 3,4-diehlorbenzyl-dimethylamine is reacted with chloroacetic acid-3-trifluoromethyl-4-chloroanilide.