CH212286A - Process for the preparation of 3-oxy-4-carbaminyl-benzene-1-arsic acid. - Google Patents
Process for the preparation of 3-oxy-4-carbaminyl-benzene-1-arsic acid.Info
- Publication number
- CH212286A CH212286A CH212286DA CH212286A CH 212286 A CH212286 A CH 212286A CH 212286D A CH212286D A CH 212286DA CH 212286 A CH212286 A CH 212286A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- oxy
- benzene
- carbaminyl
- preparation
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 241000224489 Amoeba Species 0.000 description 1
- 206010001986 Amoebic dysentery Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000224467 Giardia intestinalis Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241001180364 Spirochaetes Species 0.000 description 1
- 241000223104 Trypanosoma Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal cyanate Chemical class 0.000 description 1
- XKNKHVGWJDPIRJ-UHFFFAOYSA-N arsanilic acid Chemical compound NC1=CC=C([As](O)(O)=O)C=C1 XKNKHVGWJDPIRJ-UHFFFAOYSA-N 0.000 description 1
- 229950002705 arsanilic acid Drugs 0.000 description 1
- VJWWIRSVNSXUAC-UHFFFAOYSA-N arsinic acid Chemical class O[AsH2]=O VJWWIRSVNSXUAC-UHFFFAOYSA-N 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 208000006379 syphilis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
- C07F9/74—Aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung -von 3-Ogy-4-carbaminyl-benzol-l-arsinsäure. Die Herstellung von Carbaminobenzol- arsinsäuren, beispielsweise durch Umsetzung von Arsanilsäure mit Kaliumcyanat, ist durch das D. R. P. Nr. 213155 bekannt geworden. Von allen bisher hergestellten Carb- aminobenzolarsinsäuren konnte nur bei einer einzigen eine gewisse Wirkung auf Amöbenruhr beobachtet werden, während sie bei allen andern Infektionen, bei denen sie untersucht wurden, sämtlich versagten.
Demgegenüber wurde nun die überraschende Beobachtung gemacht, dass die 3-Oxy-4-carbaminyl-benzol-l-arsinsäure der Formel
EMI1.12
die bekannten isomeren und analogen Verbin- dungen nicht nur an Amöbenruhrwirkung übertrifft, sondern dass sie sich vor allen andern Arsinsäuren durch eine besonders ausgeprägte Wirkungsbreite auszeichnet.
So konnte zum Beispiel festgestellt werden, dass .die neue Arsinsäure bei sehr geringer Giftigkeit eine besonders auffallende Wirkung zeigt bei Kaninchensyphilis, Framboesie, Europäischer Recurrens, Hühnerspirochae- tose, Trypanosoma, Gambiense, Lamblia inte- stinalis (Maus) und Amöbenruhr (Katze).
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung der 3-Oxy-4- carbaminyl-benzol-l-arsinsäure, welches dadurch gekennzeichnet ist, dass man 3-Oxy-4- aminobenzolarsinsäure mit Cyansäure umsetzt. Die Umsetzung mit Cyansäure kann in der Weise vorgenommen werden, dass man in dem Reaktionsgemisch die Cyansäure aus Alkalicyanat durch Zusatz von Säure, wie z. B.
Essigsäure oder Salzsäure, in Freiheit setzt.
<Desc/Clms Page number 2>
Beispiel: 1,35 kg 3-Ogy-4-aminophenylarsinsäure werden in 9 Liter Wasser mit 520 cm' 42 Natronlauge gelöst, zu der Lösung werden 1,35 kg galiumcyanat gegeben und nachgerührt, bis alles gelöst ist. Man kühlt auf -[- 10 ab und lässt unter Rühren langsam 1,35 Liter Eisessig einlaufen. Nach 12 Stunden scheidet man mit Salzsäure die 3-Oxy-4- carbaminylbenzol-l-arsinsäure ab.
Die 3-Ogy-4-earbaminyl-benzol-l-arsin- säure ist ein weisses, kristallisches Pulver, schwer löslich in Wasser, unlöslich in Alkohol und Äther. Beim Erhitzen zersetzt es sich ohne zu schmelzen.
<Desc / Clms Page number 1>
Process for the preparation of 3-Ogy-4-carbaminyl-benzene-1-arsic acid. The preparation of carbaminobenzenesic acids, for example by reacting arsanilic acid with potassium cyanate, has become known from D. R. P. No. 213155. Of all the carbaminobenzenic acids so far produced, a certain effect on amoebic dysentery could only be observed in one, while they all failed in all the other infections in which they were examined.
In contrast, the surprising observation has now been made that 3-oxy-4-carbaminyl-benzene-1-arsic acid of the formula
EMI1.12
the known isomeric and analogous compounds not only surpasses amoebic agitation, but that it is characterized above all other arsinic acids by a particularly pronounced range of effects.
For example, it was found that the new arsic acid, with very low toxicity, has a particularly striking effect on rabbit syphilis, framboesia, European recurrents, chicken spirochaetes, trypanosoma, gambiense, lamblia intestinalis (mouse) and amoeba dysentery (cat).
The subject of the present patent is a process for the preparation of 3-oxy-4-carbaminyl-benzene-1-arsic acid, which is characterized in that 3-oxy-4-aminobenzolaric acid is reacted with cyanic acid. The reaction with cyanic acid can be carried out in such a way that the cyanic acid from alkali metal cyanate in the reaction mixture by adding acid, such as. B.
Acetic acid or hydrochloric acid, sets free.
<Desc / Clms Page number 2>
Example: 1.35 kg of 3-ogy-4-aminophenylarsinic acid are dissolved in 9 liters of water with 520 cm '42 sodium hydroxide solution, 1.35 kg of galium cyanate are added to the solution and stirred until everything has dissolved. It is cooled to - [- 10 and slowly poured in 1.35 liters of glacial acetic acid while stirring. After 12 hours, the 3-oxy-4-carbaminylbenzene-1-arsic acid is separated off with hydrochloric acid.
3-Ogy-4-earbaminyl-benzene-1-arsic acid is a white, crystalline powder, sparingly soluble in water, insoluble in alcohol and ether. When heated, it decomposes without melting.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE212286X | 1938-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH212286A true CH212286A (en) | 1940-11-15 |
Family
ID=5807295
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH212286D CH212286A (en) | 1938-01-15 | 1938-11-28 | Process for the preparation of 3-oxy-4-carbaminyl-benzene-1-arsic acid. |
| CH225928D CH225928A (en) | 1938-01-15 | 1938-11-28 | Process for the preparation of 3-oxy-4-carbaminylbenzene-1-arsic acid. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH225928D CH225928A (en) | 1938-01-15 | 1938-11-28 | Process for the preparation of 3-oxy-4-carbaminylbenzene-1-arsic acid. |
Country Status (2)
| Country | Link |
|---|---|
| CH (2) | CH212286A (en) |
| NL (1) | NL51617C (en) |
-
0
- NL NL51617D patent/NL51617C/xx active
-
1938
- 1938-11-28 CH CH212286D patent/CH212286A/en unknown
- 1938-11-28 CH CH225928D patent/CH225928A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH225928A (en) | 1943-02-28 |
| NL51617C (en) | 1900-01-01 |
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