CH199683A - Process for the preparation of sulfanilic acid-4-aminoanilide. - Google Patents

Process for the preparation of sulfanilic acid-4-aminoanilide.

Info

Publication number
CH199683A
CH199683A CH199683DA CH199683A CH 199683 A CH199683 A CH 199683A CH 199683D A CH199683D A CH 199683DA CH 199683 A CH199683 A CH 199683A
Authority
CH
Switzerland
Prior art keywords
aminoanilide
acid
preparation
sulfanilic acid
phenylenediamine
Prior art date
Application number
Other languages
German (de)
Inventor
F Hoffmann- Aktiengesellschaft
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of CH199683A publication Critical patent/CH199683A/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

      Verfabren    zur     Darstellung    von     Sulfauilsäure-4-aminoanilid.            Es    wurde gefunden, dass     Anilide    der       Sulfanilsäure    aus     aromatischen    Diaminen in       vivo    eine hervorragende Wirkung ,gegen       Streptokokken    aufweisen.     Anilide    der     iSulf-          anilsäure    aus aromatischen Diaminen waren  bisher nicht bekannt.

   Ihre     Herstellung    er  folgt     -durch    Einwirkung von     Acetylsulfanil-          säurehalogeniden    auf aromatische Diamine  oder auf     Monoacetylverbin.dungen    von aro  matischen     Diaminen    und     nachheriger    Ab  spaltung     .der        Acetylgruppen    oder durch Um  setzung von     Acetylsulfanilsäurehalogeniden     mit aromatischen Nitroaminen,     Reduktion     und Abspaltung der     Acetylgruppen.     



  Gegenstand     -des    vorliegenden     Patentes    ist  ein Verfahren zur Darstellung von     Sulfanil-          säure-4-aminoanilid,        welches    dadurch ge  kennzeichnet ist,     dass    man ein     Acylsulfanil-          säurehalogenicl    auf     p-Phenylendiamin    ein  wirken lässt und im so erhaltenen Produkt  die Asylgruppe     abspaltet.     



  Das     Sulfanilsäure-4-aminoanilid    schmilzt  bei<B>138'.</B> Es     ist    ziemlich löslich in Alkohol    und Methylalkohol und löst     sich    leicht     in     Säuren und Laugen. Die neue Verbindung  soll als     Arzneimittel    verwendet werden.

      <I>Beispiel:</I>  Zu<B>100</B>     Teilen,        in    200 Teilen     Wasser    ge  löstem     p-Phenylendiamin    gibt man     unter     gutem Rühren     langsam    40 Teile wenig  feuchtes     Propionylsulfanilsäureohlorid.    Nach  Beendigung der Umsetzung wird das rohe  Kondensationsprodukt mit 15 %     iger    Salz  säure :gekocht.

   Nach dem     Erkalten    saugt  man das in Salzsäure schwer     lösliche          Dihydrochlorid    des     Di-(p-amino-benzosulfo-          nyl)-p-phenylendiamins    ab und     gewinnt        das     in Salzsäure sehr leicht lösliche     Sulfanil-          säure-4-aminoanilid    durch Neutralisieren mit  Alkalien.



      Procedure for the preparation of sulfauilic acid-4-aminoanilide. It has been found that anilides of sulfanilic acid from aromatic diamines have an excellent effect in vivo against streptococci. Anilides of isulfanilic acid from aromatic diamines have not been known to date.

   They are produced by the action of acetylsulfanilic acid halides on aromatic diamines or on monoacetyl compounds of aromatic diamines and subsequent cleavage of the acetyl groups or by reaction of acetylsulfanilic acid halides with aromatic nitroamines, reduction and cleavage of the acetyl groups.



  The subject of the present patent is a process for the preparation of sulfanilic acid-4-aminoanilide, which is characterized in that an acylsulfanilic acid halogenicl is allowed to act on p-phenylenediamine and the asylum group is split off in the product thus obtained.



  The sulfanilic acid-4-aminoanilide melts at <B> 138 '. </B> It is quite soluble in alcohol and methyl alcohol and easily dissolves in acids and alkalis. The new compound is intended to be used as a medicine.

      <I> Example: </I> To <B> 100 </B> parts of p-phenylenediamine dissolved in 200 parts of water, 40 parts of a little moist propionylsulfanilic acid chloride are slowly added with thorough stirring. After the reaction has ended, the crude condensation product is boiled with 15% hydrochloric acid.

   After cooling, the dihydrochloride of di- (p-amino-benzosulphonyl) -p-phenylenediamine, which is sparingly soluble in hydrochloric acid, is suctioned off and the sulphanilic acid-4-aminoanilide, which is very easily soluble in hydrochloric acid, is obtained by neutralization with alkalis.

 

Claims (1)

PATENTANSPRUCI3 Verfahren zur Darstellung von Sulfanil- säure--l-aminoanilid, dadurch gekennzeichnet, dass man ein Acylsulfanilsäurehalogenid auf p-Phenylendiamin einwirken läBt und im so erhaltenen Produkt die Acylgruppe abspaltet. PATENT CLAIM3 Process for the preparation of sulfanilic acid - l-aminoanilide, characterized in that an acylsulfanilic acid halide is allowed to act on p-phenylenediamine and the acyl group is split off in the product thus obtained. Das Sulfanilsäure-4-aminoanilid schmilzt bei<B>138'.</B> Es ist ziemlich löslich in Alkohol und Methylalkohol und löst sich leicht in Säuren und Laugen. Die neue Verbindung soll als Arzneimittel verwendet werden. The sulfanilic acid-4-aminoanilide melts at <B> 138 '. </B> It is quite soluble in alcohol and methyl alcohol and easily dissolves in acids and alkalis. The new compound is intended to be used as a medicine.
CH199683D 1936-05-28 1936-11-05 Process for the preparation of sulfanilic acid-4-aminoanilide. CH199683A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH191673T 1936-05-28
CH199683T 1936-11-05

Publications (1)

Publication Number Publication Date
CH199683A true CH199683A (en) 1938-08-31

Family

ID=25722160

Family Applications (1)

Application Number Title Priority Date Filing Date
CH199683D CH199683A (en) 1936-05-28 1936-11-05 Process for the preparation of sulfanilic acid-4-aminoanilide.

Country Status (1)

Country Link
CH (1) CH199683A (en)

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