CH155449A - Process for the preparation of 2-oxyacetic acid benzimidazole-5-arsic acid. - Google Patents
Process for the preparation of 2-oxyacetic acid benzimidazole-5-arsic acid.Info
- Publication number
- CH155449A CH155449A CH155449DA CH155449A CH 155449 A CH155449 A CH 155449A CH 155449D A CH155449D A CH 155449DA CH 155449 A CH155449 A CH 155449A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- arsic
- preparation
- benzimidazole
- oxyacetic
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 4
- 229940106681 chloroacetic acid Drugs 0.000 claims description 4
- 238000005245 sintering Methods 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000004552 water soluble powder Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 2
- 150000001495 arsenic compounds Chemical class 0.000 description 2
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- AYPSHJCKSDNETA-UHFFFAOYSA-N 2-chloro-1h-benzimidazole Chemical compound C1=CC=C2NC(Cl)=NC2=C1 AYPSHJCKSDNETA-UHFFFAOYSA-N 0.000 description 1
- BPXINCHFOLVVSG-UHFFFAOYSA-N 9-chloroacridine Chemical compound C1=CC=C2C(Cl)=C(C=CC=C3)C3=NC2=C1 BPXINCHFOLVVSG-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- VJWWIRSVNSXUAC-UHFFFAOYSA-N arsinic acid Chemical compound O[AsH2]=O VJWWIRSVNSXUAC-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von 2-Ogyessigsäurebenzimidazol-ö-arsinsäure. Es wurde gefunden, dass sich Benzimid- azolarsinsäuren mit Halogenessigsäuren in glatter Reaktion zu 2-Oxyessigsäurebenzimid- azolarsinsäuren umsetzen lassen.
Dieser Reaktionsverlauf ist überraschend, da das Benzimidazolon sich im allgemeinen wie das Acridon verhält, beispielsweise bei der Um setzung mit Halogenphosphor-Verbindungen, das in seiner Reaktionsfähigkeit dem 9-Chlor- acridin durchaus entsprechende Chlorbenzimid- azol bildet, und bei der Einwirkung zum Beispiel von Chloressigsäure auf Acridon eine Umsetzung nicht eintritt, so dass das gleiche für das Benzimidazolon zu erwarten gewesen wäre.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung von 2-Oxy- essigsäurebenzimidazol-5-arsinsäure, welches dadurch gekennzeichnet ist, dass man Benz- imidazolon-5-arsinsäure mit Halogenessig säure umsetzt.
Das neue Verfahrensprodukt ist ein weisses, wasserlösliches Pulver, das sich beim Erhit zen nach vorherigem Sintern bei etwa 275 C zersetzt. Es findet als Heilmittel oder als Zwischenprodukt für die Herstellung von Heilmitteln Verwendung.
<I>Beispiel:</I> 43 gr Benzimidazolon-5-arsinsäure werden in<B>100</B> cm3 Wasser und 41;5 ein' Natronlauge (40 B6) gelöst, 16 gr Chloressigsäure zuge geben und 1l/2 Stunden am Rückflusskühler gekocht. Dann gibt man weitere 16 gr Chlor essigsäure und 29 cm' Natronlauge zu und kocht nochmals eine Stunde. Hierauf wird abgekühlt und angesäuert.
Von dem hierbei abgeschiedenen unveränderten Ausgangsstoff saugt man ab und scheidet die im Filtrat befindliche Arsinsäure in Form ihrer Arseno- verbindung mittelst unterphosphoriger Säure ab. Die gewaschene Arsenoverbindung wird in wenig Wasser verteilt und durch Zusatz von Ammoniak gelöst. Diese Lösung oxydiert man in bekannter Weise, scheidet dann mit- telst Salzsäure die 2-Oxyessigsäureberrzimid- azol-5-arsinsäure ab. Sie ist ein weisses, in Wasser lösliches Pulver.
Beim Erhitzen tritt nach vorherigem Sintern bei etwa<B>275'</B> Zer setzung ein.
Process for the preparation of 2-ogyacetic acid benzimidazole-ö-arsic acid. It has been found that benzimidazolaric acids can be reacted with haloacetic acids in a smooth reaction to form 2-oxyacetic acid benzimidazolaric acids.
This course of the reaction is surprising, since the benzimidazolone generally behaves like the acridone, for example when reacting with halophosphorus compounds, the reactivity of which forms chlorobenzimidazole corresponding to the 9-chloro acridine, and when exposed to, for example Chloroacetic acid does not react on acridone, so the same would have been expected for the benzimidazolone.
The present invention relates to a process for the preparation of 2-oxy-acetic acid benzimidazole-5-arsic acid, which is characterized in that benzimidazolone-5-arsic acid is reacted with haloacetic acid.
The new process product is a white, water-soluble powder that decomposes when heated after previous sintering at about 275 C. It is used as a remedy or as an intermediate in the manufacture of medicines.
<I> Example: </I> 43 grams of benzimidazolone-5-arsic acid are dissolved in <B> 100 </B> cm3 of water and 41; 5 of a sodium hydroxide solution (40 B6), 16 grams of chloroacetic acid are added and 1l / 2 Boiled for hours on the reflux condenser. Then add another 16 grams of chloroacetic acid and 29 cm of sodium hydroxide solution and cook for another hour. It is then cooled and acidified.
The unchanged starting material which has been separated out is suctioned off and the arsinic acid in the filtrate is separated off in the form of its arsenic compound by means of hypophosphorous acid. The washed arsenic compound is distributed in a little water and dissolved by adding ammonia. This solution is oxidized in a known manner, then the 2-oxyacetic acid berzimidazole-5-arsinic acid is separated off by means of hydrochloric acid. It is a white powder that is soluble in water.
During heating, after previous sintering, decomposition occurs at about <B> 275 '</B>.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE155449X | 1930-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH155449A true CH155449A (en) | 1932-06-30 |
Family
ID=5677021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH155449D CH155449A (en) | 1930-07-22 | 1931-07-14 | Process for the preparation of 2-oxyacetic acid benzimidazole-5-arsic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH155449A (en) |
-
1931
- 1931-07-14 CH CH155449D patent/CH155449A/en unknown
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