CH105106A - Process for the preparation of an alkoxyakridine. - Google Patents
Process for the preparation of an alkoxyakridine.Info
- Publication number
- CH105106A CH105106A CH105106DA CH105106A CH 105106 A CH105106 A CH 105106A CH 105106D A CH105106D A CH 105106DA CH 105106 A CH105106 A CH 105106A
- Authority
- CH
- Switzerland
- Prior art keywords
- yellow
- dilute
- acid
- ether
- needles
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229960000583 acetic acid Drugs 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 229910045601 alloy Inorganic materials 0.000 claims 1
- 239000000956 alloy Substances 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 239000012022 methylating agents Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 5
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- LUNYUJAHLUUSPX-UHFFFAOYSA-N 1,2-dimethoxyacridine Chemical compound C1=CC=CC2=CC3=C(OC)C(OC)=CC=C3N=C21 LUNYUJAHLUUSPX-UHFFFAOYSA-N 0.000 description 1
- XHIOFZCZDWVYPM-UHFFFAOYSA-N 3,6-dimethoxyacridine Chemical compound COC=1C=CC2=CC3=CC=C(C=C3N=C2C=1)OC XHIOFZCZDWVYPM-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 102100033979 Protein strawberry notch homolog 1 Human genes 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 206010013023 diphtheria Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/06—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung eines Alkoxyakridins. Es wurde gefunden, dass man 3,6-Dioxy- akridin (Benda, B. 45, S. 17041912) durch Einwirkung von Methylierungsmitteln in den 0-Dimethyläther überführen kann, ohne dabei gleichzeitig den Ringstickstoff zu alkylieren.
Das neue Produkt eignet sich infolge seiner Ungiftigkeit und starken bakterienhemmenden Wirkung zur Verhütung und Heilung von In fektionen verschiedener Art. Der Dimethyl- äther des 3,6-Dioxyakridins, der sich im Tier versuch als nahezu ungiftig erwiesen hat, hemmt z. B. das Wachstum von Diphterie- bazillen und Streptokokken noch in sehr grosser Verdünnung, während das 3,6-Dioxyakridin, selbst in starker Konzentration, fast wirkungs los ist.
Auch der 0-Monomethyläther des 3,6-Di- oxyakridins, der sich neben dem Dimethyläther in wechselnden Mengen bildet, ist ein wert volles Desinfektions- und Heilmittel. <I>Beispiel:</I> 211 gr 3,6-Dioxy akridin werden in 2000 ccm Wasser unter Zusatz von 80 gr Ätznatron ge löst. Diese Lösung wird unter Rühren all- mählich mit 266 gr Dimethylsulfat versetzt.
Man rührt, bis das Dimethylstilfat verschwun den und die Lösung nahezu neutral geworden ist, fügt dann nochmals 25 gr Dimethylsulfat und 16 gr Ätznatron, gelöst in wenig Wasser, zu und filtriert nach Beendigung der Reaktion das ausgeschiedene 3,6-Dimethoxyakridin ab. Die Rohbase wird in heisser, verdünnter Salz säure gelöst. Aus der filtrierten Lösung kri stallisiert das Chlorhydrat beim Abkühlen in wenig gefärbten Nädelchen aus.
Aus dem Chlorhydrat gewinnt man in üblicher Weise die freie Base.- In der alkalischen Mutterlauge befindet sich der Monometbyläther des 3,6-Dioxyakri- dins. Man gewinnt ihn aus der Lösung durch genaues Neutralisieren mit Essigsäure.
Das 3,6-Dimethoxyakridin (Ci sHi sNOs) kristallisiert aus .Äther in feinen, schwach gelblichen Nadeln oder dicken, hellgelben Kri stallen vom Schmelzpunkt 138-139 (unkorr) aus. Es ist leicht löslich in warmem Äther, Alkohol, Methylalkohol, Benzol und Aceton, wenig löslich in heissem Wasser, unlöslich in verdünnten Alkalien und Alkalikarbonaten. Die Lösung in konzentrierter Schwefels < i,ure ist gelb und zeigt stark grüne Fluoreszenz.
In Eisessig und in heissen verdünnten Mineral säuren löst sich Dimethoxyakridin leicht mit gelber Farbe und grüner Fluoreszenz; auf Zusatz von verdünnter überschüssiger Mineral säure kristallisieren die betreffenden Salze in Form gelber Nadeln aus.
Process for the preparation of an alkoxyakridine. It has been found that 3,6-dioxy acridine (Benda, B. 45, p. 17041912) can be converted into 0-dimethyl ether by the action of methylating agents without alkylating the ring nitrogen at the same time.
The new product is suitable due to its non-toxicity and strong bacteria-inhibiting effect for the prevention and healing of infections of various kinds. The dimethyl ether of 3,6-Dioxyakridins, which has proven to be almost non-toxic in animal experiments, inhibits z. B. the growth of diphtheria bacilli and streptococci is still very much diluted, while 3,6-dioxyakridine, even in high concentrations, is almost ineffective.
The 0-monomethyl ether of 3,6-dioxyacridine, which is formed in varying amounts in addition to the dimethyl ether, is also a valuable disinfectant and remedy. <I> Example: </I> 211 grams of 3,6-dioxy acridine are dissolved in 2000 ccm of water with the addition of 80 grams of caustic soda. This solution is gradually mixed with 266 grams of dimethyl sulfate while stirring.
The mixture is stirred until the dimethyl stilfate has disappeared and the solution has become almost neutral, then another 25 grams of dimethyl sulfate and 16 grams of caustic soda, dissolved in a little water, are added and the 3,6-dimethoxyacridine which has separated out is filtered off after the reaction has ended. The raw base is dissolved in hot, dilute hydrochloric acid. From the filtered solution, the hydrated chloride crystallizes out in little colored needles on cooling.
The free base is obtained from the chlorohydrate in the usual way. The monomethyl ether of 3,6-dioxyakridine is in the alkaline mother liquor. It is recovered from the solution by precisely neutralizing it with acetic acid.
The 3,6-dimethoxyakridine (Ci sHi sNOs) crystallizes out. Ether in fine, pale yellowish needles or thick, light yellow crystals with a melting point of 138-139 (uncorr). It is easily soluble in warm ether, alcohol, methyl alcohol, benzene and acetone, slightly soluble in hot water, insoluble in dilute alkalis and alkali carbonates. The solution in concentrated sulfuric acid is yellow and shows strong green fluorescence.
In glacial acetic acid and in hot diluted mineral acids, dimethoxyacridine dissolves easily with a yellow color and green fluorescence; Upon addition of dilute excess mineral acid, the salts concerned crystallize out in the form of yellow needles.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH105106T | 1923-04-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH105106A true CH105106A (en) | 1924-06-02 |
Family
ID=4363986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH105106D CH105106A (en) | 1923-04-14 | 1923-04-14 | Process for the preparation of an alkoxyakridine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH105106A (en) |
-
1923
- 1923-04-14 CH CH105106D patent/CH105106A/en unknown
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