CH194681A - Process for the preparation of sulfanilic acid-4-aminoanilide. - Google Patents

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

Info

Publication number
CH194681A
CH194681A CH194681DA CH194681A CH 194681 A CH194681 A CH 194681A CH 194681D A CH194681D A CH 194681DA CH 194681 A CH194681 A CH 194681A
Authority
CH
Switzerland
Prior art keywords
aminoanilide
acid
preparation
sulfanilic acid
sulfanilic
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 CH194681A publication Critical patent/CH194681A/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

  

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

       Ihre    Herstellung er  folgt durch Einwirkung von     Acylsulfanil-          säurehalogeniden    auf aromatische Diamine  oder auf     Monoacylverbindungen    von aroma  tischen Diaminen und     naehherige    Abspal  tung .der     Acylgruppe    oder durch Umsetzung  von     Acylsulfanilsäurehalogeniden    mit aroma  tischen Nitroaminen, Reduktion und Ab  spaltung der     Acylgruppe.     



  Gegenstand des. vorliegenden Patentes ist  ein- Verfahren zur Darstellung von     Sulfanil-          säure-4-aminoa.nilid,        welches    dadurch ge  kennzeichnet ist, dass man ein     Acylsulfanil-          säurebalogenid    auf     p-Phenylendiamin    ein  wirken lässt und im so erhaltenen Produkt  die     Aeylgruppe    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.         Beispiel:       Zu 11/2     Mol.        p-Phenylen.diamin    in wässe  riger Lösung wird unter Rühren 1     Mol     rohes,     feuchtes        Acetylsulfanil.säurechlorid     gegeben. Durch langsamen Zusatz von Na  tronlauge wird die Umsetzung zu     Ende    ge  führt.

   Dann gibt man.     Natronlauge    im Über  schuss hinzu, filtriert und fällt das Konden  sationsprodukt mit Salzsäure.  



  Durch Kochen mit 15 %     iger    Salzsäure  wird die     Acetylgruppe    abgespalten. Man er  hält neben wenig     Di,(p-aminobenzolsulfonyl)-          p-phenylendiamin    das-     Sulfanilsäure-4-amino-          anilid,    das aus Wasser     umkristallisiert.  



  Process for the preparation of sulfanilic acid-4-aminoanilide. It has been found that anilides of sulfanilic acid from aromatic diamines have an excellent effect against streptococci in vivo. Anilides of @ sulfanilic acid from aromatic diamines were not previously known.

       They are produced by the action of acylsulfanilic acid halides on aromatic diamines or on monoacyl compounds of aromatic diamines and subsequent cleavage of the acyl group or by reaction of acylsulfanilic acid halides with aromatic nitroamines, reduction and cleavage of the acyl group.



  The subject of the present patent is a process for the preparation of sulfanilic acid 4-aminoa.nilide, which is characterized in that an acylsulfanilic acid halide is allowed to act on p-phenylenediamine and the aeyl 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. Example: 1 mole of crude, moist acetylsulfanil acid chloride is added to 11/2 moles of p-phenylenediamine in aqueous solution with stirring. The reaction is brought to the end by the slow addition of sodium hydroxide solution.

   Then you give. Add excess sodium hydroxide solution, filter and precipitate the condensation product with hydrochloric acid.



  The acetyl group is split off by boiling with 15% hydrochloric acid. In addition to a little di, (p-aminobenzenesulfonyl) - p-phenylenediamine, he keeps the sulfanilic acid 4-amino anilide, which recrystallizes from water.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Sulfanil- säure-4-aminoanilid, dadurch gekennzeich net, dass man ein Acylsulfanilsäurehalogenid auf p-Phenylendiamin einwirken lässt und im :so erhaltenen Produkt die Acylgruppe abspaltet. Das, SulfaniLäure-4-aminoanilid schmilzt bei 138 . Es ist ziemlich löslich in Alkohol und Methylalkohol und löst sich leicht in Säuren und Laugen.. Die neue Verbindung soll als Arzneimittel verwendet werden. PATENT CLAIM: Process for the preparation of sulfanilic acid-4-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. The sulfanic acid-4-aminoanilide melts at 138. It is quite soluble in alcohol and methyl alcohol and easily dissolves in acids and alkalis .. The new compound is said to be used as a medicine.
CH194681D 1936-05-28 1936-05-28 Process for the preparation of sulfanilic acid-4-aminoanilide. CH194681A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH191673T 1936-05-28
CH194681T 1936-05-28

Publications (1)

Publication Number Publication Date
CH194681A true CH194681A (en) 1937-12-15

Family

ID=25722154

Family Applications (1)

Application Number Title Priority Date Filing Date
CH194681D CH194681A (en) 1936-05-28 1936-05-28 Process for the preparation of sulfanilic acid-4-aminoanilide.

Country Status (1)

Country Link
CH (1) CH194681A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109081793A (en) * 2018-09-28 2018-12-25 吉首大学 Sulfonamides urease inhibitor and its preparation method and purposes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109081793A (en) * 2018-09-28 2018-12-25 吉首大学 Sulfonamides urease inhibitor and its preparation method and purposes

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