CH117894A - Process for the preparation of the symmetrical urea of p-oxy-m-aminophenylarsinic acid. - Google Patents
Process for the preparation of the symmetrical urea of p-oxy-m-aminophenylarsinic acid.Info
- Publication number
- CH117894A CH117894A CH117894DA CH117894A CH 117894 A CH117894 A CH 117894A CH 117894D A CH117894D A CH 117894DA CH 117894 A CH117894 A CH 117894A
- Authority
- CH
- Switzerland
- Prior art keywords
- oxy
- acid
- preparation
- aminophenylarsinic
- aminophenylarsinic acid
- Prior art date
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Verfahren zur Darstellung des symmetrischen Harnstoffes der p-Oxy-m-amino-phenylarsinsäure. Fargher (Journ. of the Chem. Soc. <B>115</B> [1919] s.
991) erhielt bei der Behandlung von p-Oxy-m-amino-phenylarsinsäure in al kalischer Lösung mit Phosgen, in Toluol gelöst, bei 0 0 die 1 # 2-Dihydrobenzoxazolon- 4-arsinsäure mit einem Arsengehalt von 28,6 % (Theorie 28,9 %).
Überraschenderweise wurde nun gefunden, dass man bei der Einwirkung von Phosgen auf die p-Oxy-m-amino-phenylarsinsäure in alkalischer Lösung in der Wärme zweck mässig bei Temperaturen von 50-60 0, den symmetrischen Harnstoff der p-Oxy-m-amino- phenylarsinsäure erhält mit dem 30,2 0% Arsen (Theorie 30,4%). Die Verbindung entspricht der Formel
EMI0001.0030
und soll zu therapeutischen Zwecken, insbe sondere zur Bekämpfung der Spirillosen, dienen.
Sie besitzt beispielsweise der p-Oxy-m- acetyl-amino-phenylarsinsäure gegenüber, eine beständigere Wirksamkeit und einen höheren chemotherapeutischen Index, da keine Ver- seifung im Organismus erfolgt.
Beispiel: Lässt man auf 7,9 gr p-Oxy-m-amino- phenylarsinsäure (Ber. 45, 757) bei etwa 50 0 in alkalischer Lösung, zweckmässig unter Zusatz von Natriumacetat und Turbinieren, Phosgen einwirken, bis die Diazotierbarkeit verschwunden ist, so erhält man beim An säuern der Lösung den symmetrischen Harnstoff derp-Oxy-m-amino-phenylar sinsäure,
der nach gründlichem Waschen und Um kristallisieren aus heissem Wasser einen gelblich-weissen Körper darstellt. Er ist lös lich in Alkalien, unlöslich in den gebräuch lichen organischen Lösungsmitteln.
Process for the preparation of the symmetrical urea of p-oxy-m-aminophenylarsinic acid. Fargher (Journ. Of the Chem. Soc. <B> 115 </B> [1919] s.
991) when p-oxy-m-aminophenylarsinic acid was treated in alkaline solution with phosgene, dissolved in toluene, at 0 0 1 # 2-dihydrobenzoxazolone-4-arsinic acid with an arsenic content of 28.6% (theory 28.9%).
Surprisingly, it has now been found that when phosgene acts on the p-oxy-m-aminophenylarsinic acid in alkaline solution in the heat, expediently at temperatures of 50-60 0, the symmetrical urea of the p-oxy-m-amino - Phenylarsinic acid contains the 30.2 0% arsenic (theory 30.4%). The compound corresponds to the formula
EMI0001.0030
and should be used for therapeutic purposes, in particular special to combat spirillosis.
Compared to p-oxy-m-acetyl-aminophenylarsinic acid, for example, it has a more stable effectiveness and a higher chemotherapeutic index, since there is no saponification in the organism.
Example: If phosgene is allowed to act on 7.9 g of p-oxy-m-aminophenylarsinic acid (Ber. 45, 757) at about 50 ° in an alkaline solution, expediently with the addition of sodium acetate and turbination, until the diazotizability has disappeared, when acidifying the solution, the symmetrical urea derp-oxy-m-aminophenylaric acid is obtained,
which after thorough washing and recrystallization from hot water turns into a yellowish-white body. It is soluble in alkalis and insoluble in the common organic solvents.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE117894X | 1924-07-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH117894A true CH117894A (en) | 1926-12-01 |
Family
ID=5655363
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH117894D CH117894A (en) | 1924-07-02 | 1925-06-15 | Process for the preparation of the symmetrical urea of p-oxy-m-aminophenylarsinic acid. |
Country Status (2)
Country | Link |
---|---|
AT (1) | AT105092B (en) |
CH (1) | CH117894A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE849697C (en) * | 1942-07-14 | 1952-09-18 | Hoechst Ag | Process for the preparation of 3-carbamino-4-oxy-5-iodo-benzaric acid |
-
1925
- 1925-06-15 CH CH117894D patent/CH117894A/en unknown
- 1925-06-24 AT AT105092D patent/AT105092B/en active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE849697C (en) * | 1942-07-14 | 1952-09-18 | Hoechst Ag | Process for the preparation of 3-carbamino-4-oxy-5-iodo-benzaric acid |
Also Published As
Publication number | Publication date |
---|---|
AT105092B (en) | 1926-12-27 |
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