CH199910A - Process for the preparation of N-methylsulfanilic acid-4-aminoanilide. - Google Patents

Process for the preparation of N-methylsulfanilic acid-4-aminoanilide.

Info

Publication number
CH199910A
CH199910A CH199910DA CH199910A CH 199910 A CH199910 A CH 199910A CH 199910D A CH199910D A CH 199910DA CH 199910 A CH199910 A CH 199910A
Authority
CH
Switzerland
Prior art keywords
acid
aminoanilide
methylsulfanilic
preparation
catalyst
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 CH199910A publication Critical patent/CH199910A/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

Landscapes

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

Description

  

      Verfahren    zur Darstellung von     N-Nethylsulfanilsäure-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        Aminen    waren  bisher nicht bekannt.

   Ihre Darstellung kann  dadurch erfolgen, dass man     Acylsulfanil-          säurehalogenide    auf aromatische Diamine  oder     Monoacylverbindungen    von aromati  schen Aminen     einwirken    lässt und die     Acyl-          gruppen    abspaltet oder     Acylsulfanilsäure-          halogenide    mit aromatischen     Nitroaminen     umsetzt, reduziert und die     Acylgruppen    ab  spaltet.  



  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Darstellung von     N-Methyl-          sulfanilsäure-4-aminoanilid,    welches dadurch  gekennzeichnet ist, dass man ein     p-Halogen-          benzolsulfonsäure-4-acylaminoanilid    mit Mo  nomethylamin in     Gegenwart    von Katalysa  toren, wie Naturkupfer oder Kupfersalzen,  zum     N-Methylsulfanilsäure-4-acylaminoani-          lid    umsetzt und die     Acylgruppe    abspaltet.

      Das     N-Methylsulfanilsäure-4-aminoanilid     schmilzt bei 191 bis<B>192'.</B> Es ist unlöslich  in kaltem und heissem Wasser, ziemlich lös  lich. in Äthyl- und Methylalkohol, leicht lös  lich in     Mineralsäuren    und     Alkalilaugen.    Die  neue     Verbindung    soll als     Arzneimittel    ver  wendet werden.  



  <I>Beispiel:</I>  6 Teile     p-Chlorbenzolsulfonsäure-4-acet-          aminoanilid    (hergestellt aus     p-Chlorbenzol-          sulfochlorid    und     p-Aminoacetanilid,    F. P.  201 bis 202  ), 0,5 Teile Naturkupfer C und  50 Teile 30%ige     Monomethylaminlösung     werden auf 170 bis 175   erhitzt, dann fügt  man Natronlauge im     Überschuss    zu,     filtriert     und kocht     1/s        Stunde.    Die erkaltete Lösung  wird nochmals filtriert und das Filtrat durch  Säurezusatz neutralisiert.

   Das rohe     N-Methyl-          sulfanilsäure-4-aminoanilid    wird aus ver  dünntem Methylalkohol umkristallisiert.



      Process for the preparation of N-methylsulfanilic 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 amines were not previously known.

   They can be prepared by letting acylsulfanilic acid halides act on aromatic diamines or monoacyl compounds of aromatic amines and splitting off the acyl groups or reacting acylsulfanilic acid halides with aromatic nitroamines, reducing them and splitting off the acyl groups.



  The present patent is a process for the preparation of N-methylsulfanilic acid-4-aminoanilide, which is characterized in that one p-halobenzenesulfonic acid-4-acylaminoanilide with Monomethylamine in the presence of catalysts, such as natural copper or copper salts , converts to N-methylsulfanilic acid-4-acylaminoanilide and splits off the acyl group.

      The N-methylsulfanilic acid-4-aminoanilide melts at 191 to <B> 192 '. </B> It is insoluble in cold and hot water, quite soluble. in ethyl and methyl alcohol, easily soluble in mineral acids and alkaline solutions. The new compound is intended to be used as a drug.



  <I> Example: </I> 6 parts of p-chlorobenzenesulphonic acid-4-acet-aminoanilide (made from p-chlorobenzenesulphochloride and p-aminoacetanilide, FP 201 to 202), 0.5 parts of natural copper C and 50 parts of 30% ige monomethylamine solution are heated to 170 to 175, then sodium hydroxide solution is added in excess, filtered and boiled for 1 / s hour. The cooled solution is filtered again and the filtrate is neutralized by adding acid.

   The crude N-methylsulfanilic acid 4-aminoanilide is recrystallized from dilute methyl alcohol.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von N-Methyl- sulfanilsäure-4-aminoanilid, dadurch gekenn- zeichnet, daB man ein p-Halogenbenzolsul- fonsäure-4-acylaminoanilid mit Monomethyl- amin in Gegenwart eines Katalysators um setzt und aus dem so erhaltenen Produkt die Acylgruppe abspaltet. Das N-Methylsulfanilsäure-4-aminoanilid schmilzt bei 191 bis<B>192</B> . PATENT CLAIM: Process for the preparation of N-methylsulfanilic acid-4-aminoanilide, characterized in that a p-halobenzenesulfonic acid-4-acylaminoanilide is reacted with monomethylamine in the presence of a catalyst and the product thus obtained is converted into the Cleaving acyl group. The N-methylsulfanilic acid-4-aminoanilide melts at 191 to 192. Es ist unlöslich in kaltem und heissem Wasser, ziemlich löslich in Athyl- und Methylalkohol, leicht löslich in Mineralsäuren und Alkalilaugen. Die neue Verbindung soll als Arzneimittel verwendet werden. UNTERANSPRVCHE 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Katalysator Naturkupfer verwendet. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Katalysator ein Kupfersalz verwendet. It is insoluble in cold and hot water, fairly soluble in ethyl and methyl alcohol, slightly soluble in mineral acids and alkaline solutions. The new compound is intended to be used as a medicine. SUB-CLAIM 1. Method according to patent claim, characterized in that natural copper is used as the catalyst. 2. The method according to claim, characterized in that a copper salt is used as the catalyst.
CH199910D 1937-02-19 1937-02-19 Process for the preparation of N-methylsulfanilic acid-4-aminoanilide. CH199910A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH199910T 1937-02-19

Publications (1)

Publication Number Publication Date
CH199910A true CH199910A (en) 1938-09-15

Family

ID=4442066

Family Applications (1)

Application Number Title Priority Date Filing Date
CH199910D CH199910A (en) 1937-02-19 1937-02-19 Process for the preparation of N-methylsulfanilic acid-4-aminoanilide.

Country Status (1)

Country Link
CH (1) CH199910A (en)

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