CH199686A - Process for the preparation of N-methylsulfanilic acid-4-aminoanilide. - Google Patents

Process for the preparation of N-methylsulfanilic acid-4-aminoanilide.

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Publication number
CH199686A
CH199686A CH199686DA CH199686A CH 199686 A CH199686 A CH 199686A CH 199686D A CH199686D A CH 199686DA CH 199686 A CH199686 A CH 199686A
Authority
CH
Switzerland
Prior art keywords
acid
aminoanilide
catalyst
preparation
methyl
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 CH199686A publication Critical patent/CH199686A/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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung von     N-Rethylsulfanilsäure-4-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 Aminen waren  bisher nicht bekannt.

   Ihre Darstellung kann  dadurch     erfolgen,        dass    man     Acylsulfanil-          säurehalogenide    auf aromatische Diamine  oder     Monoacylverbindungen    von aromatischen  Aminen     einwirken    lässt und .die Asylgruppen       abspaltet    oder     Acylsulfanilsäurehalogenide     mit aromatischen     Nitroaminen    umsetzt, redu  ziert und die Asylgruppen abspaltet.  



  Gegenstand     .des    vorliegenden     Patentes        ist     ein Verfahren zur Darstellung von     N-Me-          thylsulfanilsäure-4-aminoanilid,    welches da  durch gekennzeichnet ist,     @dass    man ein     N,N-          Acyl-methylsulfanilsäureamid    mit     p-Halogen-          nitrobenzol    mit Hilfe von Katalysatoren,     wie     Naturkupfer oder Kupferbronze, zum     N,

  N-          Acyl-methylsulfanilsäure=4-nitroanilid    um  setzt und in beliebiger     Reihenfolge    die Nitro-         gruppe    reduziert und die     Asylgruppe    ab  spaltet.  



  Das     N-Methylsulfanilsäure-4-aminoanilid     schmilzt bei     191-19,2'.    Es     ist    unlöslich in  kaltem und heissem Wasser, ziemlich löslich  in Äthyl- und Methylalkohol, leicht     löslieh     in Mineralsäuren und     Alkalilaugen.    Die neue       Verbindung    soll als     Arzneimittel    verwendet  werden.  



  <I>Beispiel:</I>  20 Teile     N,N-Acetylmethylsulfani1säure-          amid,    15 Teile     p-Chlornitrobenzol,    10 Teile       Kaliumkarbonat    und 1 Teil Naturkupfer C  werden     auf        etwa    200' erhitzt. Nach dem  Erkalten     digeriert    man mit     $00    Teilen       5%iger    Kalilauge und filtriert.

   Das     Filtrat          wird    angesäuert und das ausfallende     Kon-          densationsprodukt    mit 100     Teilen        10%iger          Natronlauge    gekocht. Beim Neutralisieren  mit     verdünnter    Salzsäure fällt das     N-Metlhyl-          sulfanilsäure-4-nitroanilid    aus.

   Es wird aus  Methylalkohol     umkristallisiert    und     schmilzt     bei<B>1810.</B>      10 Teile     dieses        Nitroanilids        werden    in     200     Teilen     Methylalkohol        unter        Zusatz    eines       Nickelkatalysators    bei<B>70--80'</B>     mit    Wasser  stoff geschüttelt. Wenn die     Wasserstoffauf-          nahme        beendigt    ist,     filtriert    man den Kata  lysator ab.

   Nach dem Abdampfen     des    Me  thylalkohols     hinterbleibt    das     N-Methylsulf-          anilsäure-4-aminoanilid.  



  Process for the preparation of N-Rethylsulfanilic acid-4-aminoanilide. It has been found that anilides of sulfanilic acid from aromatic diamines have an excellent effect in vivo against streptococci. Anilides of sulfanilic acid from aromatic amines were not previously known.

   They can be represented by letting acylsulfanilic acid halides act on aromatic diamines or monoacyl compounds of aromatic amines and splitting off the asylum groups or reacting and reducing acylsulfanilic acid halides with aromatic nitroamines and splitting off the asylum groups.



  The subject of the present patent is a process for the preparation of N-methylsulfanilic acid-4-aminoanilide, which is characterized by that an N, N-acyl-methylsulfanilic acid amide with p-halo-nitrobenzene with the aid of catalysts such as Natural copper or copper bronze, for N,

  N-acylmethylsulfanilic acid = 4-nitroanilide converts and in any order the nitro group is reduced and the asylum group is split off.



  The N-methylsulfanilic acid-4-aminoanilide melts at 191-19.2 '. It is insoluble in cold and hot water, fairly soluble in ethyl and methyl alcohol, easily soluble in mineral acids and alkaline solutions. The new compound is intended to be used as a medicine.



  <I> Example: </I> 20 parts of N, N-acetylmethylsulfaniic acid amide, 15 parts of p-chloronitrobenzene, 10 parts of potassium carbonate and 1 part of natural copper C are heated to about 200 '. After cooling, it is digested with $ 00 parts of 5% potassium hydroxide solution and filtered.

   The filtrate is acidified and the condensation product which precipitates is boiled with 100 parts of 10% strength sodium hydroxide solution. When neutralizing with dilute hydrochloric acid, the N-methylsulfanilic acid 4-nitroanilide precipitates.

   It is recrystallized from methyl alcohol and melts at <B> 1810. </B> 10 parts of this nitroanilide are shaken with hydrogen in 200 parts of methyl alcohol with the addition of a nickel catalyst at <B> 70-80 '</B>. When the uptake of hydrogen has ceased, the catalyst is filtered off.

   After the methyl alcohol has evaporated, the N-methylsulfanilic acid 4-aminoanilide remains.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von N-Methyl- sulfanilsä.ure-4-aminoanilid, dadurch gekenn zeichnet, dass man ein N,N-Acyl-methyl- sulfanilsäureamid mit p-Halogennitrobenzol mit Hilfe eines Katalysators umsetzt und in dem so erhaltenen Produkt in beliebiger Reihenfolge die Nitrogruppe reduziert und die Acylgruppe abspaltet. Das N-Methyls@ulfanilsäure-4-aminoa, PATENT CLAIM: A process for the preparation of N-methyl-sulfanilsä.ure-4-aminoanilide, characterized in that an N, N-acyl-methyl-sulfanilic acid amide is reacted with p-halonitrobenzene with the aid of a catalyst and in the product thus obtained in in any order, the nitro group is reduced and the acyl group is split off. The N-methyls @ ulfanilic acid-4-aminoa, nilicl schmilzt bei 191-192'. Es ist unlöslich in kaltem und heissem Wasser, ziemlich löslich in Äthyl- und Methylalkohol, leicht löslich in Mineralsäuren und Alkalilaugen. Die neue Verbindung soll als Arzneimittel verwendet werden. UNTERANSPRüCHE: 1. nilicl melts at 191-192 '. It is insoluble in cold and hot water, fairly soluble in ethyl and methyl alcohol, easily soluble in mineral acids and alkaline solutions. The new compound is intended to be used as a medicine. SUBCLAIMS: 1. Verfahren nach Patentanspruch. dadurch gekennzeichnet, da.B man als Katalysator Naturkupfer verwendet. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Katalysator Kupferbronze verwendet. Method according to claim. characterized in that natural copper is used as the catalyst. 2. The method according to claim, characterized in that the catalyst used is copper bronze.
CH199686D 1937-01-11 1937-01-11 Process for the preparation of N-methylsulfanilic acid-4-aminoanilide. CH199686A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH194885T 1937-01-11
CH199686T 1937-01-11

Publications (1)

Publication Number Publication Date
CH199686A true CH199686A (en) 1938-08-31

Family

ID=25722712

Family Applications (1)

Application Number Title Priority Date Filing Date
CH199686D CH199686A (en) 1937-01-11 1937-01-11 Process for the preparation of N-methylsulfanilic acid-4-aminoanilide.

Country Status (1)

Country Link
CH (1) CH199686A (en)

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