CH153965A - Process for the preparation of a 2-oxymethylbenzimidazole arsic acid. - Google Patents
Process for the preparation of a 2-oxymethylbenzimidazole arsic acid.Info
- Publication number
- CH153965A CH153965A CH153965DA CH153965A CH 153965 A CH153965 A CH 153965A CH 153965D A CH153965D A CH 153965DA CH 153965 A CH153965 A CH 153965A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- glycolic acid
- preparation
- arsic
- diamino
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 208000000230 African Trypanosomiasis Diseases 0.000 claims description 2
- 241000223105 Trypanosoma brucei Species 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 235000010265 sodium sulphite Nutrition 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000035876 healing Effects 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung einer 2-Ogymethylbenzimidazol-arsinsäure. Es wurde gefunden, dass man 2-Oxyme- thylbenzimidazolarsinsäuren der folgenden Formel
EMI0001.0004
erhalten kann, wenn man o-Diaminobenzol- arsinsäuren mit Glykolsäure behandelt.
- Die Reaktion kann beispielsweise - in der Weise ausgeführt werden, dass man eine o-Diamino- benzolarsinsäure und Glykolsäure zusammen schmilzt, oder dass man die Arsinsäure mit einer wässerigen, vorzugsweise konzentrierten Lösung der Glykolsäure erhitzt. In letzterem Falle hat es sich als vorteilhaft erwiesen, die Reaktion in Gegenwart einer Mineralsäure, z. B. konzentrierter Salzsäure, auszuführen.
Die neuen 2-Oxymethylbenzimidazolai-sin- säuren sind therapeutisch wertvolle Verbin dungen, die beispielsweise gegen Nagana und Recurrens sehr wirksam sind. Die Verbindungen bilden mit Alkalien und organischen Basen Salze, deren Lösun gen, besonders wenn man eine geringe Menge Natriumsulfit hinzufügt, beständig sind.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung einer 2-Oxy- methylbenzimidazolarsinsäure, welches da durch gekennzeichnet ist, dass man 3.4-Di- aminobenzol-l-arsinsäure mit Glykolsäure um setzt.
<I>Beispiele:</I> 1. 46,4 gr 3.4-Diaminobenzol-l-arsinsäure werden mit 38 gr kristallisierter Glykolsäure oder der entsprechenden Menge konzentrierter wässeriger Glykolsäurelösung innig vermischt und im Ölbad auf<B>1100</B> erhitzt, bei welcher Temperatur Umsetzung erfolgt und unter Aufschäumen die Reaktionsmasse allmählich erstarrt. Man nimmt in etwa 300 cm' heissem Wasser auf, klärt mit Tierkohle und scheidet durch Abkühlen die 2 - Oxymelhylbenzimid- azolarsinsäure ab, die aus verdünnter Natrium acetatlösung umkristallisiert wird. Ausbeute 30 gr, F. unscharf 210-215o C unter Zer setzung.
Schwer löslich in Wasser, löslich in Methyl- und Äthylalkohol, unlöslich in Ace ton und Äther.
2. 40 gr 3.4-Diaminobenzol-l-arsinsäure werden in 300 eins Salzsäure (spez. Gewicht 1,08) gelöst, 30 gr einer 70 %igen Glykol- säurelösung zugegeben und 1 Stunde am Rückfluss gekocht. Die dunkel gefärbte Lö sung wird mit Reinigungskohle filtriert und mit Natronlauge kongoneutral abgestumpft. Die abgeschiedene 2-Ogymethylbenzimidazol- arsinsäure wird abgesaugt und aus verdünn ter Natriumacetatlösung umkristallisiert.
Aus beute etwa 25 gr. Die Eigenschaften sind dieselben wie unter Beispiel 1 angegeben.
Process for the preparation of a 2-ogymethylbenzimidazole arsic acid. It has been found that 2-oxymethylbenzimidazolar acids of the following formula
EMI0001.0004
can be obtained when treating o-diaminobenzenesic acids with glycolic acid.
The reaction can, for example, be carried out in such a way that an o-diaminobenzolaric acid and glycolic acid are melted together, or that the arsic acid is heated with an aqueous, preferably concentrated, solution of glycolic acid. In the latter case it has proven advantageous to carry out the reaction in the presence of a mineral acid, e.g. B. concentrated hydrochloric acid.
The new 2-oxymethylbenzimidazoleic acids are therapeutically valuable compounds that are very effective against Nagana and recurrences, for example. The compounds form salts with alkalis and organic bases, the solutions of which are stable, especially if a small amount of sodium sulfite is added.
The present invention relates to a process for preparing a 2-oxymethylbenzimidazolaric acid, which is characterized in that 3,4-diaminobenzene-1-arsic acid is reacted with glycolic acid.
<I> Examples: </I> 1. 46.4 grams of 3,4-diaminobenzene-l-arsinic acid are intimately mixed with 38 grams of crystallized glycolic acid or the corresponding amount of concentrated aqueous glycolic acid solution and heated to <B> 1100 </B> in an oil bath the temperature at which the reaction takes place and the reaction mass gradually solidifies with foaming. It is taken up in about 300 cm 'of hot water, clarified with animal charcoal and, by cooling, the 2-oxymelhylbenzimidazolaric acid is separated off, which is recrystallized from dilute sodium acetate solution. Yield 30 gr, F. unsharp 210-215o C with decomposition.
Slightly soluble in water, soluble in methyl and ethyl alcohol, insoluble in acetone and ether.
2. 40 grams of 3,4-diaminobenzene-l-arsic acid are dissolved in 300 liters of hydrochloric acid (specific weight 1.08), 30 grams of a 70% glycolic acid solution are added and the mixture is refluxed for 1 hour. The dark-colored solution is filtered with cleaning charcoal and truncated with sodium hydroxide solution. The separated 2-Ogymethylbenzimidazol- arsinsäure is filtered off with suction and recrystallized from dilute sodium acetate solution.
From booty about 25 gr. The properties are the same as given in Example 1.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE153965X | 1930-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH153965A true CH153965A (en) | 1932-04-15 |
Family
ID=5676075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH153965D CH153965A (en) | 1930-04-29 | 1931-03-31 | Process for the preparation of a 2-oxymethylbenzimidazole arsic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH153965A (en) |
-
1931
- 1931-03-31 CH CH153965D patent/CH153965A/en unknown
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