CH199684A - Process for the preparation of sulfanilic acid-3-aminoanilide. - Google Patents

Process for the preparation of sulfanilic acid-3-aminoanilide.

Info

Publication number
CH199684A
CH199684A CH199684DA CH199684A CH 199684 A CH199684 A CH 199684A CH 199684D A CH199684D A CH 199684DA CH 199684 A CH199684 A CH 199684A
Authority
CH
Switzerland
Prior art keywords
aminoanilide
sulfanilic acid
preparation
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 CH199684A publication Critical patent/CH199684A/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-3-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     Aoetylsulfanil-          sä.urehalogeniden    auf     aromatische    Diamine  oder auf     Monoacetylverbindungen    von aroma  tischen Diaminen und     naohheriger    Abspal  tung 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-3-aminoanilid,    welches dadurch ge  kennzeichnet ist, dass man ein     Acylsulfanil-          säurehalogenid    auf ein     Monoacyl-meta-phe-          nylendiamin    einwirken lässt und im so er  haltenen Produkt die     Acylgruppen    ab  spaltet.

      Das     Sulfanilsäure-3-aminoanilid    schmilzt  bei     158-160'.    Es ist ziemlich löslich in  Alkohol     und.    Methylalkohol und löst     sieh     leicht in Säuren und Laugen. Die neue Ver  bindung soll als     Arzneimittel    verwendet  werden.    <I>Beispiel:</I>    30 Teile fast trockenes     PropionyIsulfanil-          säurechlorid    werden mit 50' Teilen     m-Amino-          acetanilid    durch     gelindes    Erwärmen in 1.00  Teilen Methylalkohol umgesetzt.

   Das Kon  densationsprodukt wird durch Kochen mit  150 Teilen 15%iger     Salzsäure        verseift.    Man  erhält das     Sulfanilsäure-3-aminoanilid    vom  F.     P.158-160     .



  Process for the preparation of sulfanilic acid-3-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 aoetylsulfanil acid halides on aromatic diamines or on monoacetyl compounds of aromatic diamines and closer elimination of the acetyl groups or by reaction of acetylsulphanilic acid halides with aromatic nitroamines, reduction and elimination of the acetyl groups.



  The subject of the present patent is a process for the preparation of sulfanilic acid-3-aminoanilide, which is characterized in that an acylsulfanilic acid halide is allowed to act on a monoacyl-meta-phenylenediamine and the acyl groups are removed in the product obtained in this way splits.

      The sulfanilic acid 3-aminoanilide melts at 158-160 '. It is quite soluble in alcohol as well. Methyl alcohol and easily dissolves in acids and alkalis. The new connection is intended to be used as a drug. <I> Example: </I> 30 parts of almost dry propionyl isulphanilic acid chloride are reacted with 50 parts of m-aminoacetanilide in 1.00 parts of methyl alcohol by gentle heating.

   The condensation product is saponified by boiling with 150 parts of 15% hydrochloric acid. The sulfanilic acid 3-aminoanilide of F.P. 158-160 is obtained.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Sulfanil- säure-3-aminoanilid, dadurch gekennzeichnet, dass man ein Aoylsulfanilsäurehalogenid auf ein Monoa.cyl-meta-phenylendiamin einwir- ken läBt und im so erhaltenen Produkt die Acylgruppen abspaltet. PATENT CLAIM: Process for the preparation of sulfanilic acid 3-aminoanilide, characterized in that an aoylsulfanilic acid halide is allowed to act on a mono-acyl-meta-phenylenediamine and the acyl groups are split off in the product thus obtained. Das Sulfanilsäure-3-aminoanilid schmilzt bei<B>158--1-60'.</B> Es ist ziemlich löslich in Alkohol und Methylalkohol und löst sich leicht in Säuren und Laugen. Die neue Ver bindung soll als Arzneimittel verwendet werden. The sulfanilic acid 3-aminoanilide melts at <B> 158--1-60 '. </B> It is quite soluble in alcohol and methyl alcohol and easily dissolves in acids and alkalis. The new connection is intended to be used as a drug.
CH199684D 1936-05-28 1936-11-05 Process for the preparation of sulfanilic acid-3-aminoanilide. CH199684A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH191673T 1936-05-28
CH199684T 1936-11-05

Publications (1)

Publication Number Publication Date
CH199684A true CH199684A (en) 1938-08-31

Family

ID=25722161

Family Applications (1)

Application Number Title Priority Date Filing Date
CH199684D CH199684A (en) 1936-05-28 1936-11-05 Process for the preparation of sulfanilic acid-3-aminoanilide.

Country Status (1)

Country Link
CH (1) CH199684A (en)

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