CH194685A - Process for the preparation of sulfanilic acid-4-dimethyl-aminoanilide. - Google Patents

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

Info

Publication number
CH194685A
CH194685A CH194685DA CH194685A CH 194685 A CH194685 A CH 194685A CH 194685D A CH194685D A CH 194685DA CH 194685 A CH194685 A CH 194685A
Authority
CH
Switzerland
Prior art keywords
dimethyl
aminoanilide
sulfanilic acid
acid
preparation
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 CH194685A publication Critical patent/CH194685A/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-dimethyl-aminoanllid.       Es wurde gefunden, dass     Anilide    der     Sulf-          a.nilsäure        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    Abspal  tung der     Acylgruppe.     



  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Darstellung von     Sulfanil-          säure-4-dimethyl-aminoanilid,    welches da  durch gekennzeichnet ist, dass man ein     Acyl-          sulfanilsäurehalogenid    auf     4-,Aminodimethyl-          anilin    einwirken lässt und im so erhaltenen  Produkt die     Acylgruppe        abspaltet.     



  Das,     Sulfanilsäure-4-dimethyl-aminoani-          lid    schmilzt bei 231     bis-   <B>232'</B> C. Es ist ziem  lich schwer löslich in Alkohol und Methyl-         alkohol    und löst sich leicht     in.    Säuren und  Laugen. Die neue Verbindung soll als Arz  neimittel verwendet werden.  



  <I>Beispiel:</I>  60 Teile     4-Aminodimethylanilin    werden  in     wässeriger    Lösung mit 200     Teilen    rohem,  feuchten     Propionylsulfanilsäurechlorid    ge  mischt und nach     und    nach ein     Überschuss    von  Natronlauge zugegeben.

   Die alkalische Lö  sung wird     filtriert    und     .das    Kondensations  produkt durch Zusatz von :Säure zur Ab  scheidung gebracht.     Zur        Ab-bpaltung    der       Acetylgruppe    wird es mit 500     Teilen,    15 %     -          igerSalzsäure    gekocht. Die     entstandene    klare  Lösung     des    Hydrochlorids     wird    neutralisiert,  wobei das     Sulfanilsäure-4-dimethyl-amino-          anilid    ausfällt.



  Process for the preparation of sulfanilic acid-4-dimethyl-amino-amide. It has been found that anilides of sulf-a.nilic 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 present patent relates to a process for the preparation of sulfanilic acid 4-dimethylaminoanilide, which is characterized in that an acylsulfanilic acid halide is allowed to act on 4-, aminodimethylaniline and the acyl group is split off in the product thus obtained.



  The, sulfanilic acid-4-dimethyl-aminoanilid melts at 231 to- <B> 232 '</B> C. It is not very soluble in alcohol and methyl alcohol and easily dissolves in acids and alkalis. The new compound is intended to be used as a drug.



  <I> Example: </I> 60 parts of 4-aminodimethylaniline are mixed in aqueous solution with 200 parts of crude, moist propionylsulfanilic acid chloride and an excess of sodium hydroxide solution is gradually added.

   The alkaline solution is filtered and the condensation product separated by adding: acid. To split off the acetyl group, it is boiled with 500 parts of 15% hydrochloric acid. The resulting clear solution of the hydrochloride is neutralized, whereby the sulfanilic acid 4-dimethylamino anilide precipitates.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von ;Sulfanil- säure-4-dimethyl-aminoanilid,dadurch ge kennzeichnet, dass man ein Acylsulfanilsäure- halogenid auf 4-Aminodimethylanilin ein- wirken läU und im so erhaltenen Produkt die Acylgruppe abspaltet. Das .Sulfanilsäure-4-dimethyl-aminoanilid schmilzt bei<B>231</B> bis 232' C. Es ist ziemlich schwer 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-dimethyl-aminoanilide, characterized in that an acylsulfanilic acid halide is allowed to act on 4-aminodimethylaniline and the acyl group is split off in the product thus obtained. The .sulfanilic acid-4-dimethyl-aminoanilide melts at <B> 231 </B> to 232 ° C. It is rather sparingly soluble in alcohol and methyl alcohol and easily soluble in acids and alkalis. The new compound is intended to be used as a medicine.
CH194685D 1936-05-28 1936-05-28 Process for the preparation of sulfanilic acid-4-dimethyl-aminoanilide. CH194685A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH191673T 1936-05-28
CH194685T 1936-05-28

Publications (1)

Publication Number Publication Date
CH194685A true CH194685A (en) 1937-12-15

Family

ID=25722158

Family Applications (1)

Application Number Title Priority Date Filing Date
CH194685D CH194685A (en) 1936-05-28 1936-05-28 Process for the preparation of sulfanilic acid-4-dimethyl-aminoanilide.

Country Status (1)

Country Link
CH (1) CH194685A (en)

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