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.

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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
Application number
Other languages
German (de)
Inventor
Chemische Fabrik Auf Schering
Original Assignee
Chem Fab Vorm E Schering
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chem Fab Vorm E Schering filed Critical Chem Fab Vorm E Schering
Publication of CH117894A publication Critical patent/CH117894A/en

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  • 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)

PATENTANSPRUCH: Verfahren zur Darstellung des symme trischen Harnstoffes der p-Oxy-m-amino- phenylarsinsäure, dadurch gekennzeichnet, dass man auf die p-Oxy-m-amino-phenylarsin- säure in alkalischer Lösung in der Wärme Phosgen einwirken lässt. Die neue Verbindung stellt, aus heissem Wasser umkristallisiert, einen gelblich-weissen Körper dar, der in Alkalien löslich, in den gebräuchlichen organischen Lösungsmitteln dagegen unlöslich "ist ; sie soll zu therapeu- tischen Zwecken, insbesondere zur Be kämpfung der Spirillosen dienen. PATENT CLAIM: Process for the preparation of the symmetrical urea of p-oxy-m-aminophenylarsinic acid, characterized in that phosgene is allowed to act on the p-oxy-m-aminophenylarsinic acid in an alkaline solution in the heat. Recrystallized from hot water, the new compound represents a yellowish-white body that is soluble in alkalis but insoluble in common organic solvents. It is intended to serve therapeutic purposes, in particular to combat spirillosis. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man Phosgen bei Tempe raturen von<B>50-600</B> einwirken lässt. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that phosgene is allowed to act at temperatures of <B> 50-600 </B>.
CH117894D 1924-07-02 1925-06-15 Process for the preparation of the symmetrical urea of p-oxy-m-aminophenylarsinic acid. CH117894A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (1)

* Cited by examiner, † Cited by third party
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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