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
Links
- -1 acridinium compound Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 150000001875 compounds Chemical group 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- 150000001251 acridines Chemical class 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- 230000002421 anti-septic effect Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 231100000053 low toxicity Toxicity 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZHSKUOZOLHMKEA-UHFFFAOYSA-N 4-[5-[bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]butanoic acid;hydron;chloride Chemical compound Cl.ClCCN(CCCl)C1=CC=C2N(C)C(CCCC(O)=O)=NC2=C1 ZHSKUOZOLHMKEA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- GXHNEVACDYVJNL-UHFFFAOYSA-N [N].C1=CC=CC2=CC3=CC=CC=C3N=C21 Chemical compound [N].C1=CC=CC2=CC3=CC=CC=C3N=C21 GXHNEVACDYVJNL-UHFFFAOYSA-N 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
Landscapes
- 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)
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) |
-
1923
- 1923-10-23 CH CH108488D patent/CH108488A/en unknown
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