CH108488A - Process for the preparation of an acridinium compound. - Google Patents

Process for the preparation of an acridinium compound.

Info

Publication number
CH108488A
CH108488A CH108488DA CH108488A CH 108488 A CH108488 A CH 108488A CH 108488D A CH108488D A CH 108488DA CH 108488 A CH108488 A CH 108488A
Authority
CH
Switzerland
Prior art keywords
compound
preparation
easily soluble
dioxyakridine
compounds
Prior art date
Application number
Other languages
German (de)
Inventor
Leopold Cassella Co Ge Haftung
Original Assignee
Cassella Leopold & Co Gmbh
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 Cassella Leopold & Co Gmbh filed Critical Cassella Leopold & Co Gmbh
Publication of CH108488A publication Critical patent/CH108488A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B15/00—Acridine dyes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung einer     Akridiniumverbindung.       Es wurde gefunden, dass man     Oxyakri-          dine,    wie zum Beispiel 3,6 -     Dioxyakridin     (Benda., B.     Ber.    45, 1704j1912) am     Akridin-          stickstoff        alkylieren    kann, ohne gleichzeitig  die     Hydroxy        lgruppe    zu     alkylieren,    wobei man       -ezeie,huet,eAntise#ptika,erhä,1t.    Gegenstand  <B>i</B> tus,  des vorliegenden Patentes ist nun ein Ver  fahren zur     Herstellung    von     3,

  6-Dioxy-10-          methylakridiniumchlorid,    darauf beruhend,  dass man     3,6-Dioxyakridin    bei Abwesenheit  säurebindender Stoffe mit     Methylierungsmit-          teln        behandelt.     



  Die neue -     Oxyakridiniumverbindung    ist  infolge ihrer starken bakteriziden     Kraft        und     ihrer geringen Giftigkeit ein ausgezeichnetes  Antiseptikum; sie zeigt kaum Farbstoff  charakter, wodurch sie sich von den entspre  chenden     Aminoakridiniumverbindungen    vor  teilhaft unterscheidet. Gegenüber den     Akri-          dinverbindungen    der Patente Nr. 105106;  105865 und 105866 besitzt sie den Vorzug  grösserer Löslichkeit und Diffusionsfähigkeit.

         Beispiel:     80     Liter    Nitrobenzol werden auf<B>180'</B> er  hitzt, .dann 8,4 kg     Dioxyakridin    zugegeben,    worauf     die    Temperatur fällt. Nachdem sie  wieder auf<B>170</B> bis<B>180'</B> gestiegen ist, wer  den 12 kg :geschmolzener     p-Toluolsulfosäur.e-          methylester        hinzugegeben    und noch 15 Mi  nuten zum Sieden erhitzt. Unter     Braunf        Ir-          bung    geht das     Dioxyakridin        allmählich    in  Lösung.  



  Die Lösung wird 12     Stunden    stehen ge  lassen. Das Reaktionsprodukt scheidet sich  als braune Kristallmasse .ab, die .abgesaugt  wird. Nach dem Auswaschen mit wenig  Äther werden die     Kristalle    mit 5     Liter        Salz-          säure    (roh) und 200 Liter Wasser     längere     Zeit gekocht,     bis    sich die     Toluolsulfosäure-          verbindung        in    das     Chlormethylat    umgewan  delt hat, dann heiss filtriert und letzteres mit  Salzsäure oder Kochsalz gefällt.

   Durch noch  maliges     Umlösen    aus Wasser erhält man die  Verbindung in gelben Nadeln, die in Natron  lauge spielend leicht löslich sind.  



       Aus    dem     nitrobenzolhaltigen    Filtrat der       Alkylierung    können weitere Mengen des  Produktes gewonnen werden.



  Process for the preparation of an acridinium compound. It has been found that oxyakridines such as 3,6-dioxyakridine (Benda., B. Ber. 45, 1704j1912) can be alkylated on the acridine nitrogen without alkylating the hydroxyl group at the same time, with -ezeie, huet, eAntise # ptika, get, 1t. The subject of the present patent is now a process for the production of 3,

  6-Dioxy-10-methylakridinium chloride, based on the fact that 3,6-Dioxyakridine is treated with methylating agents in the absence of acid-binding substances.



  The new - oxyakridinium compound is an excellent antiseptic due to its strong bactericidal power and low toxicity; it shows hardly any dye character, which makes it different from the corresponding Aminoakridiniumverbindungen before geous. Compared to the acridine compounds of patents No. 105106; 105865 and 105866 it has the advantage of greater solubility and diffusibility.

         Example: 80 liters of nitrobenzene are heated to <B> 180 '</B>, then 8.4 kg of dioxyakridine are added, whereupon the temperature drops. After it has risen to <B> 170 </B> to <B> 180 '</B>, the 12 kg: molten p-toluenesulfonic acid methyl ester is added and heated to the boil for another 15 minutes. The dioxyakridine gradually dissolves, turning brown.



  The solution is left to stand for 12 hours. The reaction product separates out as a brown crystal mass which is sucked off. After washing with a little ether, the crystals are boiled with 5 liters of hydrochloric acid (raw) and 200 liters of water for a long time until the toluenesulfonic acid compound has converted into chloromethylate, then filtered while hot and the latter is precipitated with hydrochloric acid or common salt.

   By dissolving it again from water, the compound is obtained in yellow needles, which are easily soluble in sodium hydroxide solution.



       Further amounts of the product can be obtained from the nitrobenzene-containing filtrate from the alkylation.

Claims (1)

PATUNTANSPRUCH: Verfahren zur Darstellung einer Akridi- niumverbindung, darin bestehend, @dass man ,:,6-Dioxyakridin <B>0</B> bei Abwesenheit säurebin- dender Stoffe mit 111ethylierungsmitteln be handelt. Die Verbindung bildet gelbe Nadeln, die in heissem Wasser leicht, in kaltem Was ser schwer, in Natronlauge spielend leicht löslich sind. Claim to the patent: Process for the preparation of an acridinium compound, consisting in that:, 6-Dioxyakridine <B> 0 </B> is treated with ethylating agents in the absence of acid-binding substances. The compound forms yellow needles, which are easily soluble in hot water, difficult in cold water and easily soluble in sodium hydroxide solution. Die neue Oxyakridiniumverbindung ist infolge ihrer starken bakteriziden Kraft und ihrer geringen Giftigkeit ein ausgezeichnetes Antiseptikum; sie zeigt kaum Fa.rbstoff charakter, wodurch sie sich von den entspre chenden Aminoa.kridiniumverbindungen vor- teilhaTt unterscheidet. Gegenüber den Akri- diniumverbindungen der Patente Nr. 105106, 105865 und 105866 besitzt sie den Vorzug grösserer Löslichkeit und Diffusionsfähigkeit. The new oxyakridinium compound is an excellent antiseptic because of its strong bactericidal power and low toxicity; it shows hardly any dye character, which is why it differs advantageously from the corresponding amino-cridinium compounds. Compared to the acridine compounds of patents 105106, 105865 and 105866, it has the advantage of greater solubility and diffusibility.
CH108488D 1923-10-23 1923-10-23 Process for the preparation of an acridinium compound. CH108488A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH108488T 1923-10-23

Publications (1)

Publication Number Publication Date
CH108488A true CH108488A (en) 1925-01-16

Family

ID=4367458

Family Applications (1)

Application Number Title Priority Date Filing Date
CH108488D CH108488A (en) 1923-10-23 1923-10-23 Process for the preparation of an acridinium compound.

Country Status (1)

Country Link
CH (1) CH108488A (en)

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