CH191673A - Process for the preparation of sulfanilic acid-4-aminoanilide. - Google Patents

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

Info

Publication number
CH191673A
CH191673A CH191673DA CH191673A CH 191673 A CH191673 A CH 191673A CH 191673D A CH191673D A CH 191673DA CH 191673 A CH191673 A CH 191673A
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 CH191673A publication Critical patent/CH191673A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides 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
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, 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     Sul-          fanilsäure    aus aromatischen Diaminen in     vivo     eine hervorragende Wirkung gegen     Strepto-          kokken    aufweisen.     Anilide    der     Sulfanilsäure     aus aromatischen Diaminen waren bisher nicht  bekannt.

   Ihre Herstellung erfolgt durch Ein  wirkung von     Acylsulfanilsäurehalogeniden    auf  aromatische Diamine oder auf     Monoäcylver-          bindungen    von aromatischen Diaminen und       nachheriger    Abspaltung der     Acylgruppen    oder  durch Umsetzung von     Acylsulfanilsäurehaloge-          niden    mit aromatischen Nitroaminen, Reduk  tion und Abspaltung der     'Acylgruppe.     



  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Darstellung von     Sulfanil-          säure-4-aminoanilid,    welches dadurch gekenn  zeichnet ist, dass man     Acylsulfanilsäurehaloge-          nid    auf     Monoacyl-p-phenylendiamin    einwirken  lässt und die     Acylgruppen    abspaltet.  



  Das     Sulfanilsäure-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.  



  <I>Beispiel:</I>  <B>150</B> Teile     Monoacetyl-p-phenylendiamin     werden in 300 Teilen Methylalkohol mit der  berechneten Menge von rohem, feuchtem     Ace-          tylsulfanilsäurechlorid    unter Zusatz von Na  tronlauge zur Reaktion gebracht. Dann gibt  man 500 Teile Wasser und Natronlauge im  Überschuss zu und filtriert das nicht umge  setzte     Monoacetyl-p-phenylendiamin    ab. Das  Filtrat wird angesäuert und das Kondensa  tionsprodukt abgesaugt. Zur Abspaltung der       Acetylgruppen    wird es 1 Stunde mit 700 Tei  len 15     o/oiger    Salzsäure gekocht.

   Die     eDt-          standene    klare Lösung des Hydrochlorids  wird neutralisiert und das     Sulfanilsäure-4-          aminoanilid    unter Zusatz von Kohle aus Was  ser umkristallisiert.



  Process for the preparation of sulfanilic acid-4-aminoanilide. It has been found that anilides of sulphanilic acid from aromatic diamines have an excellent action 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 groups 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-aminoanilide, which is characterized in that acylsulfanilic acid halide is allowed to act on monoacyl-p-phenylenediamine and the acyl groups are split off.



  The sulfanilic 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 intended to be used as a medicine.



  <I> Example: </I> <B> 150 </B> parts of monoacetyl-p-phenylenediamine are reacted in 300 parts of methyl alcohol with the calculated amount of crude, moist acetylsulfanilic acid chloride with the addition of sodium hydroxide solution. Then 500 parts of water and sodium hydroxide solution are added in excess and the unconverted monoacetyl-p-phenylenediamine is filtered off. The filtrate is acidified and the condensation product is filtered off with suction. To split off the acetyl groups, it is boiled with 700 parts of 15% hydrochloric acid for 1 hour.

   The resulting clear solution of the hydrochloride is neutralized and the sulfanilic acid-4-aminoanilide is recrystallized from water with the addition of charcoal.

Claims (1)

PATENTAXSPRUCH Verfahren zur Darstellung von Sulfanil- säure-4-aminoanilid, dadurch gekennzeichnet, dass man Acylsulfanilsäurehalogenid auf Mono- acyl-p-phenylendiamin einwirken lässt und die Acylgruppen abspaltet. Das Sulfanilsäure-4-aminoanilid schmilzt bei<B>1380.</B> Es ist ziemlich löslich in Alkohol und Methylalkohol und löst sich leicht 111 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 acylsulfanilic acid halide is allowed to act on mono-acyl-p-phenylenediamine and the acyl groups are split off. The sulfanilic acid-4-aminoanilide melts at <B> 1380. </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.
CH191673D 1936-05-28 1936-05-28 Process for the preparation of sulfanilic acid-4-aminoanilide. CH191673A (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
CH191673A true CH191673A (en) 1937-06-30

Family

ID=4437760

Family Applications (1)

Application Number Title Priority Date Filing Date
CH191673D CH191673A (en) 1936-05-28 1936-05-28 Process for the preparation of sulfanilic acid-4-aminoanilide.

Country Status (1)

Country Link
CH (1) CH191673A (en)

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