CH194683A - Process for the preparation of sulfanilic acid 2-methyl-5-aminoanilide. - Google Patents

Process for the preparation of sulfanilic acid 2-methyl-5-aminoanilide.

Info

Publication number
CH194683A
CH194683A CH194683DA CH194683A CH 194683 A CH194683 A CH 194683A CH 194683D A CH194683D A CH 194683DA CH 194683 A CH194683 A CH 194683A
Authority
CH
Switzerland
Prior art keywords
methyl
sulfanilic acid
aminoanilide
preparation
acid
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 CH194683A publication Critical patent/CH194683A/en

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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

Description

  

  Verfahren zur Darstellung von     Sulfanilsäure-2-methyl-6-aminoanilid.       Es wurde gefunden, dass     Anilide    der     Sulf-          anilsäure    aus     aromatischen    Diaminen in     vivo     eine hervorragende Wirkung gegen     @Strepto-          kokken    aufweisen.     Anilide    der     !Sulfanile.äure     aus aromatischen Diaminen waren bisher  nicht bekannt.

   Ihre     Herstellung    erfolgt durch  Einwirkung von     Acylsulfanilsäurehalogeni-          den    auf     aromatische    Diamine oder auf     Mono-          acylverbindungen    von aromatischen Diami  nen und     nachherige    Abspaltung der     Acyl-          gruppe    oder durch Umsetzung von     Acylsulf-          anilsäurehalogeniden    mit aromatischen     Ni-          troaminen,    Reduktion und Abspaltung der       Acylgruppe.     



  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur     Darstellung    von     Sulfanil-          säure-2-methyl-5-aminoanilid,        welches    da  durch gekennzeichnet ist, dass man ein     Acyl-          sulfanilsä,urehalogenid    auf ein     1-Aminoh-2-          m-ethyl@-,5-acylaminobenzdl        einwirken    lässt und  im so erhaltenen Produkt die     Acylgruppen     abspaltet.  



  Das     Sulfanilsäure-2-methyl-5-aminoanilid     schmilzt bei 205 bis<B>206'.</B> Es ist ziemlich    leicht     löelich    in Alkohol und Methylalkohol  und löst sich leicht in     ,Säuren    und Laugen.  Die neue     Verbindung    soll als Arzneimittel       verwendet    werden.  



  <I>Beispiel:</I>       2(h    Teile     1-Amino-2-methyl-5-aoetylamino-          benzol    werden in 50 Teilen Methylalkohol  mit der     berechneten    Menge von rohem,       feuchtem        Acetylsulfanilsäurechlorid    unter  Zusatz von verdünnter Natronlauge konden  siert.

   Die alkalische Lösung des     Kondensa-          tionsproduktes        wird        filtriert    und das.     Aeetyl-          sulfanilsäure-    2     -,meth)rl-w,5!##acetylaminoanilid     durch     Ansäuern    ausgefällt. Man verseift es  durch Kochen mit 15%iger Salzsäure. Das  entstehende     Sulfanilsäure-2-methyl-5-amino-          anilid    wird aus, verdünntem Methylalkohol  umkristallisiert.



  Process for the preparation of sulfanilic acid 2-methyl-6-aminoanilide. It has been found that anilides of sulphanilic 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-2-methyl-5-aminoanilide, which is characterized in that an acyl-sulfanilic acid, urehalide is added to a 1-aminoh-2- m-ethyl @ -, Lets 5-acylaminobenzdl act and splits off the acyl groups in the product thus obtained.



  The sulfanilic acid-2-methyl-5-aminoanilide melts at 205 to <B> 206 '. </B> It is quite easily 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> 2 (h parts of 1-amino-2-methyl-5-aoetylamino-benzene are condensed in 50 parts of methyl alcohol with the calculated amount of crude, moist acetylsulfanilic acid chloride with the addition of dilute sodium hydroxide solution.

   The alkaline solution of the condensation product is filtered and the acetylsulfanilic acid 2 -, meth) rl-w, 5! ## acetylaminoanilide is precipitated by acidification. It is saponified by boiling with 15% hydrochloric acid. The resulting sulfanilic acid 2-methyl-5-amino anilide is recrystallized from dilute methyl alcohol.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Sulfanil- üäure-2-methyl-5-aminoanilid, dadurch ge kennzeichnet, dass man ein Acylsulfanil- säurehalogenid auf ein 1-Amino-2-methyl-5- acylaminobenzol einwirken lässt und im so erhaltenen Produkt die Acylgruppen abspal tet. Das @Sulfanilsäure-2-methyl-5-aminoani- lid schmilzt bei 205 bis, 206 . PATENT CLAIM: Process for the preparation of sulfanilic acid-2-methyl-5-aminoanilide, characterized in that an acylsulfanilic acid halide is allowed to act on a 1-amino-2-methyl-5-acylaminobenzene and the acyl groups in the product thus obtained split off. The @sulfanilic acid-2-methyl-5-aminoanilid melts at 205 to. 206. Es ist ziemlich leicht löslich in Alkohol und Methylalkohol und löst sich leicht in Säuren und Laugen. Die neue Verbindung soll als Arzneimittel verwendet werden. It is fairly soluble in alcohol and methyl alcohol, and easily dissolves in acids and alkalis. The new compound is intended to be used as a medicine.
CH194683D 1936-05-28 1936-05-28 Process for the preparation of sulfanilic acid 2-methyl-5-aminoanilide. CH194683A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH191673T 1936-05-28
CH194683T 1936-05-28

Publications (1)

Publication Number Publication Date
CH194683A true CH194683A (en) 1937-12-15

Family

ID=25722156

Family Applications (1)

Application Number Title Priority Date Filing Date
CH194683D CH194683A (en) 1936-05-28 1936-05-28 Process for the preparation of sulfanilic acid 2-methyl-5-aminoanilide.

Country Status (1)

Country Link
CH (1) CH194683A (en)

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