CH90883A - Process for the preparation of p-arseno-di- (1-phenyl-2,3-dimethyl-4-amino-5-pyrazolone) -monoacetic acid. - Google Patents
Process for the preparation of p-arseno-di- (1-phenyl-2,3-dimethyl-4-amino-5-pyrazolone) -monoacetic acid.Info
- Publication number
- CH90883A CH90883A CH90883DA CH90883A CH 90883 A CH90883 A CH 90883A CH 90883D A CH90883D A CH 90883DA CH 90883 A CH90883 A CH 90883A
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethyl
- amino
- pyrazolone
- phenyl
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- 108010008488 Glycylglycine Proteins 0.000 description 1
- MPNZKEGCSZGKMJ-UHFFFAOYSA-N NCC(=O)O.[As] Chemical compound NCC(=O)O.[As] MPNZKEGCSZGKMJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940017705 formaldehyde sulfoxylate Drugs 0.000 description 1
- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 description 1
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung der p-Arseno-di-(1-phenyl-2.3-diiimethy1-4-amino-5-pyrilzolon)- monoessigsiinre. Im Hauptpatent wurde ein Verfahren zur Darstellung von p-Arseno-di-(1-phenyl-2-3- dimethyl-4-amino-5-pyrazolon) - monomethy- lensulfoxylsäure beschrieben, das darauf ruht, dass man p-Asseno-di-(i-phenyl-2 ³ 3-di- methyl-4i-amino-5-pyrazolon) mit Fornial- dehydsulfoxylat behandelt, wodurch die saure Atomgruppe -CH2-O-SOH eingeführt wird.
Durch diese Einführung gewinnt man eine für medizinische Zwecke wertvolle Verbindung.
Es wurde gefunden dass man durch Ein führung des Essigsäurerestes -CH2-COOH an Stelle des Methylensulfoxylrestes eine Ver bindung mit ähnlicher Wirkungsweise ge winnt. Um dieselbe herzustellen, lässt man auf p-Arseno-di-(i-Phenyl-2 ³ 3-dimethyl-4- amiho-5-pyrazolon) Halogenessigsäure, z. B. Bromessigsäure, einwirken. Die neue Ver bindung ist in Wasser schwer löslich, in Alkohol unlöslich, in Mineralsäuren und Al- kalier löst sie sich, mit den letzteren bildet sie gelbliche, leicht lösliche Salze.
Beispiel: 12,54 g salzsaures p-Arseno-cli-(1-plienyl- 2 ³3-dimethyl-4-amino-5-pyrazolon) werden in 100 cm' Wasser gelöst, mit 15%iger Na tronlauge neutralisiert und 14 g Bromessig säure, gelöst in 30 g Wasser, hinzugegeben. Man erhitzt kurze Zeit auf etwa 60 , ver dünnt dann mit Wasser und fügt Soda lösung hinzu. Von dem Ungelösten wird nun abfiltriert und die Glycinarsenoverbin- dung aus d er Lösung mit Essigsäure ge fällt.
Verwendet man in diesem Beispiel einen grösseren Überschuss an Bromessigsäure, so erhält man das dem Monoglygin ähnliche Diglycin.
Process for the preparation of the p-arseno-di- (1-phenyl-2,3-diimethy1-4-amino-5-pyrilzolone) monoacetic acids. In the main patent, a process for the preparation of p-arseno-di- (1-phenyl-2-3-dimethyl-4-amino-5-pyrazolone) - monomethylene sulfoxylic acid was described, which is based on the fact that one p-Asseno-di - (i-phenyl-2 ³ 3-dimethyl-4i-amino-5-pyrazolone) treated with formaldehyde sulfoxylate, whereby the acidic atomic group -CH2-O-SOH is introduced.
This introduction creates a connection that is valuable for medical purposes.
It has been found that by introducing the acetic acid residue -CH2-COOH instead of the methylene sulfoxyl residue, a connection with a similar mode of action is won. To prepare the same, p-arseno-di- (i-phenyl-23 3-dimethyl-4-amiho-5-pyrazolone) haloacetic acid, e.g. B. bromoacetic acid act. The new compound is sparingly soluble in water, insoluble in alcohol, it dissolves in mineral acids and alkalis, with the latter it forms yellowish, easily soluble salts.
Example: 12.54 g of hydrochloric acid p-arseno-cli- (1-plienyl- 2 ³3-dimethyl-4-amino-5-pyrazolone) are dissolved in 100 cm 'of water, neutralized with 15% sodium hydroxide solution and 14 g of bromoacetic acid acid, dissolved in 30 g of water, was added. It is heated to about 60 for a short time, then diluted with water and soda solution is added. The undissolved material is then filtered off and the glycine arsenic compound is precipitated from the solution with acetic acid.
If a larger excess of bromoacetic acid is used in this example, diglycine, which is similar to monoglygin, is obtained.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE90883X | 1917-12-15 | ||
| CH90186T | 1918-12-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH90883A true CH90883A (en) | 1921-10-01 |
Family
ID=25704132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH90883D CH90883A (en) | 1917-12-15 | 1918-12-27 | Process for the preparation of p-arseno-di- (1-phenyl-2,3-dimethyl-4-amino-5-pyrazolone) -monoacetic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH90883A (en) |
-
1918
- 1918-12-27 CH CH90883D patent/CH90883A/en unknown
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