CH199685A - Process for the preparation of N-methylsulfanilic acid-4-aminoanilide. - Google Patents

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

Info

Publication number
CH199685A
CH199685A CH199685DA CH199685A CH 199685 A CH199685 A CH 199685A CH 199685D A CH199685D A CH 199685DA CH 199685 A CH199685 A CH 199685A
Authority
CH
Switzerland
Prior art keywords
acid
aminoanilide
preparation
methylsulfanilic
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 CH199685A publication Critical patent/CH199685A/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     N-Nethylsulfanilsäure-4-aminoaniliä.            Es        wurde    gefunden, dass     Anilide    der  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 aroma  tischen Aminen einwirken lässt und die Asyl  gruppen abspaltet oder     Acylsulfanilsäure-          halogenide    mit     aromatischen    Nitroaminen  umsetzt, reduziert und die Asylgruppen ab  spaltet.  



  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-          Acylmethylsulfanilsäureamid    mit einem       Halogenacy        lanilid    mit Hilfe von Katalysa  toren, wie Naturkupfer oder Kupferbronze,  zum N,N'-Acyl-methylsulfanilsäure-4-acyl-         aminoanilid    umsetzt und die Asylgruppen  abspaltet.  



  Das     N-Methylsulfanilsäure-4-aminoanilid     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    ver  wendet werden.  



  <I>Beispiel:</I>  15 Teile     N,N-Acetyl-methylsulfanilsäure-          amid,    15 Teile     p-Bromacetanilid,    10     Teile          galiumkarbonat    und     1/-9    Teil Naturkupfer C  werden einige Zeit zum Schmelzen erhitzt.  Die erkaltete Masse wird mit 200 Teilen  10%iger Natronlauge behandelt und das       Alkaliunlösliche    durch     Filtrieren    entfernt.  Durch Neutralisieren gewinnt man das Kon  densationsprodukt. Dieses wird durch     Kochen     mit 100 Teilen 10%iger Natronlauge ver  seift.

   Das     N-Methylsulfanilsäure-4-amino-          anilid    wird am besten aus verdünntem Me  thylalkohol umkristallisiert.           PATENTANSPRUCH:     Verfahren zur Darstellung von     N.N-Me-          thylsulfanilsäure-4-aminoanilid,    dadurch ge  kennzeichnet,     daB    man ein     N,

  N-Acylmethyl-          sulfanilsäureamid    mit einem     Halogenacyl-          anilid    mit Hilfe eines     Katalysators    umsetzt  und aus dem so erhaltenen Produkt die     Acyl-          ä        ruppen    abspaltet.  



  Das     N-14lethylsulfanilsäure-4-aminoanilid          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.  



  Process for the preparation of N-methylsulfanilic acid-4-aminoaniliä. It has been found that anilides of the sulfanilic acid from aromatic diamines have an excellent effect against streptococci in vivo. 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 acylsulphanilic acid halides with aromatic nitroamines, reducing them 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 the fact that an N, N-acylmethylsulfanilic acid amide with a halogenacy lanilide with the help of catalysts, such as natural copper or copper bronze, is used for N, N'-acyl-methylsulfanilic acid-4-acyl-aminoanilide converts and splits off the asylum groups.



  The N-methylsulfanilic acid-4-aminoanilide 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 drug.



  <I> Example: </I> 15 parts of N, N-acetylmethylsulfanilic acid amide, 15 parts of p-bromoacetanilide, 10 parts of galium carbonate and 1 / -9 part of natural copper C are heated for some time to melt. The cooled mass is treated with 200 parts of 10% sodium hydroxide solution and the alkali-insoluble material is removed by filtration. The condensation product is obtained by neutralization. This is soaped by boiling with 100 parts of 10% sodium hydroxide solution.

   The N-methylsulfanilic acid-4-amino anilide is best recrystallized from dilute methyl alcohol. PATENT CLAIM: Process for the preparation of N.N-methylsulfanilic acid-4-aminoanilide, characterized in that an N,

  N-acylmethylsulfanilic acid amide is reacted with a haloacyl anilide with the aid of a catalyst and the acyl groups are split off from the product thus obtained.



  The N-14lethylsulfanilic acid 4-aminoanilide 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.

 

Claims (1)

UNTERANSPRÜCHE: 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, daB man als Katalysator Naturkupfer verwendet. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, daB man als Katalysator Kupferbronze verwendet. SUBClaims: 1. Process 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.
CH199685D 1937-01-11 1937-01-11 Process for the preparation of N-methylsulfanilic acid-4-aminoanilide. CH199685A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH194885T 1937-01-11
CH199685T 1937-01-11

Publications (1)

Publication Number Publication Date
CH199685A true CH199685A (en) 1938-08-31

Family

ID=25722711

Family Applications (1)

Application Number Title Priority Date Filing Date
CH199685D CH199685A (en) 1937-01-11 1937-01-11 Process for the preparation of N-methylsulfanilic acid-4-aminoanilide.

Country Status (1)

Country Link
CH (1) CH199685A (en)

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