CH194885A - Process for the preparation of sulfanilic acid-4-aminoanilide. - Google Patents

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

Info

Publication number
CH194885A
CH194885A CH194885DA CH194885A CH 194885 A CH194885 A CH 194885A CH 194885D A CH194885D A CH 194885DA CH 194885 A CH194885 A CH 194885A
Authority
CH
Switzerland
Prior art keywords
aminoanilide
sulfanilic acid
acid
preparation
parts
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 CH194885A publication Critical patent/CH194885A/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

Description

  

  Verfahren zur Darstellung von     Sulfanilsä.ure-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 Aminen waren bisher nicht  bekannt.  



  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Darstellung von     Sulfanil-          säure-4-acninoanilid,    welches dadurch gekenn  zeichnet ist, dass man ein     Acylsulfanilsäure-          amid    mit einem     p-Halogerracylanilid    mit Hilfe  von Katalysatoren, wie Naturkupfer oder  Kupferbronze, zum     Acylsulfanilsäure-4        acyl-          aminoanilid    umsetzt und die     Acylgruppen     abspaltet.  



  Das     Sulfanilsäure-4-aminoanilid    schmilzt  bei 138 0. Es ist ziemlich löslich in     Äthyl-          und    Methylalkohol und löst sich leicht in  Säuren und Laugen. Die neue Verbindung  soll als     Arzneimittel    verwendet werden.  



  <I>Beispiel 1:</I>  20 Teile     Acetylsulfarrilsäureamid,    20 Teile       p-Biomacetanilid,    12 Teile     Kaliumkarbonat       und 1 Teil Naturkupfer C werden gut ge  mischt auf 180-200 0 erhitzt. Nach dem Er  kalten löst man die Mischung in 300 Teilen  5     %iger        Natronlauge        und        filtriert        das        Alkali-          unlösliche    ab.

   Durch Neutralisieren erhält  man das     Acetylsulfanilsäur#e-4-acetaminoanilid,     das durch einstündiges Kochen mit 100     Tei-          len        10        %iger        Natronlauge        oder        100        Teilen          15        %iger        Salzsäure        verseift        wird.        Das        rohe          Sulfanilsäure-4-aminoanilid    wird aus Wasser       

  unterKohlezusatz    umkristallisiert. Es schmilzt  bei 137-138<B>0</B>.    <I>Beispiel: 2:</I>    30 Teile     Aoetylsulfanilsäur,eamid,    30 Teile       p-Chloracetanilid,    15 Teile     Kaliumkarbonat     und 1 Teil Naturkupfer C werden auf 180       bis    190 0 erhitzt.

   Dann wird die Mischung       mit        300        Teilen    5     %iger        Natronlauge        digeriert.     Nach dem     Abfiltrieren    eines unlöslichen Rück  standes säuert man an und kocht das aus  gefallene     Kondensationsprodukt    mit 100 Tei  len 10     %iger    Natronlauge. Das rohe Sulfanil-           säure-4-aminoariilid    wird aus Wasser umkri  stallisiert.



  Process for the preparation of 4-aminoanilide sulfanilic acid. 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 amines were not previously known.



  The subject of the present patent is a process for the preparation of sulfanilic acid-4-acninoanilide, which is characterized in that an acylsulfanilic acid amide with a p-halogerracylanilide with the aid of catalysts such as natural copper or copper bronze, to acylsulfanilic acid-4 acyl - Reacts aminoanilide and splits off the acyl groups.



  The sulfanilic acid-4-aminoanilide melts at 138 0. It is quite soluble in ethyl and methyl alcohol and easily dissolves in acids and alkalis. The new compound is intended to be used as a medicine.



  <I> Example 1: </I> 20 parts of acetylsulfaric acid amide, 20 parts of p-biomacetanilide, 12 parts of potassium carbonate and 1 part of natural copper C are mixed well and heated to 180-200 °. After cooling, the mixture is dissolved in 300 parts of 5% sodium hydroxide solution and the alkali-insolubles are filtered off.

   Acetylsulfanilic acid 4-acetaminoanilide is obtained by neutralization and is saponified by boiling for one hour with 100 parts of 10% strength sodium hydroxide solution or 100 parts of 15% strength hydrochloric acid. The crude sulfanilic acid-4-aminoanilide is made from water

  Recrystallized with the addition of carbon. It melts at 137-138 <B> 0 </B>. <I> Example: 2: </I> 30 parts of aoetylsulfanilic acid, eamide, 30 parts of p-chloroacetanilide, 15 parts of potassium carbonate and 1 part of natural copper C are heated to 180 to 190 °.

   Then the mixture is digested with 300 parts of 5% sodium hydroxide solution. After an insoluble residue has been filtered off, the mixture is acidified and the condensation product which has precipitated out is boiled with 100 parts of 10% strength sodium hydroxide solution. The crude sulfanilic acid-4-aminoariilid is recrystallized from water.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Sulfanil- säure - 4 - aminoanilid, dadurch gekennzeich net, dass man ein Acylsulfanilsäureamid mit einem p-Halogenacylanilid mit Hilfe eines Katalysators umsetzt und aus dem so erhal tenen Produkt die Acylgruppen abspaltet. Das Sulfanilsäure-4-aminoanilid schmilzt bei 138 . Es ist ziemlich löslich in Äthyl und Methylalkohol und löst sich leicht in Säuren und Laugen. Die neue Verbindung soll als Arzneimittel verwendet- werden. UNTERANSPRüCHE 1. PATENT CLAIM: Process for the preparation of sulfanilic acid - 4 - aminoanilide, characterized in that an acylsulfanilic acid amide is reacted with a p-haloacylanilide with the aid of a catalyst and the acyl groups are split off from the product obtained in this way. The sulfanilic acid 4-aminoanilide melts at 138. It is fairly soluble in ethyl and methyl alcohol and easily dissolves in acids and alkalis. The new compound is to be used as a drug. SUBCLAIMS 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Katalysator Naturkupfer verwendet. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Katalysator Kupferbronze verwendet. Process according to patent claim, characterized in that natural copper is used as the catalyst. 2. The method according to claim, characterized in that copper bronze is used as the catalyst.
CH194885D 1937-01-11 1937-01-11 Process for the preparation of sulfanilic acid-4-aminoanilide. CH194885A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH194885T 1937-01-11

Publications (1)

Publication Number Publication Date
CH194885A true CH194885A (en) 1937-12-31

Family

ID=4439657

Family Applications (1)

Application Number Title Priority Date Filing Date
CH194885D CH194885A (en) 1937-01-11 1937-01-11 Process for the preparation of sulfanilic acid-4-aminoanilide.

Country Status (1)

Country Link
CH (1) CH194885A (en)

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