CH194684A - Process for the preparation of sulfanilic acid-3-aminoanilide. - Google Patents

Process for the preparation of sulfanilic acid-3-aminoanilide.

Info

Publication number
CH194684A
CH194684A CH194684DA CH194684A CH 194684 A CH194684 A CH 194684A CH 194684D A CH194684D A CH 194684DA CH 194684 A CH194684 A CH 194684A
Authority
CH
Switzerland
Prior art keywords
aminoanilide
acid
preparation
sulfanilic acid
acyl
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 CH194684A publication Critical patent/CH194684A/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-3-aminoanilid.       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-          säurehalogeni4en    auf aromatische Diamine  oder auf     Monoacylverbindungen    von aroma  tischen Diaminen und     nachherige    Abspal  tung der     Acylgruppe    oder durch Umsetzung  von     Acylsulfanileäurehalogeniden    mit aro  matischen Nitroaminen,     Reduktion    und Ab  spaltung der     Acylgruppe.     



  Gegenstand des vorliegenden     Patentes    ist  ein     Verfahren    zur Darstellung von     Sulfanil-          säure-3-aminoanilid,    welches dadurch ge  kennzeichnet ist,     :dass    man ein     Acylsulfanil-          säurehalogenid    auf ein     Mono-acyl-meta-phe-          nylendiamin    einwirken lässt und im so er  haltenen Produkt .die     Acylgruppen    abspaltet.  



  Das     Sulfanilsäure-.3-aminoanilid    schmilzt  bei 158 bis<B>160'.</B> Es ist ziemlich löslich in  Alkohol und Methylalkohol und löst sich    leicht in Säuren und Laugen. Die neue Ver  bindung soll als     Arzneimittel    verwendet  werden.  



  <I>Beispiel;</I>  40 Teile     Monoacetyl-m-phenylendiamin-          hydrochlorid    werden in     wässeriger    Lösung  mit     @d-er        berechneten    Menge von rohem,  feuchtem     Acetylsulfanilsäurechlorid        versetzt.     Durch langsamen Zusatz von     verdünnter     Natronlauge wird die Kondensation bewirkt.  Die alkalische Lösung wird filtriert und das       Kondensationsprodukt        @dureh    Säurezusatz  ausgefällt.

   Das     Acetylsulfanilsäure-3-acetyl-          aminoanilid    wird zur Abspaltung .der     Ace-          tylgruppen    mit 2.50 Teilen 15 %     iger    Salz  säure gekocht. Die Lösung     des,        Hydrochlo-          rids    wird     neutralisiert,    das auskristallisie  rende     Sulfanilsäure-3-aminoanilid    abgesaugt  und     auG    Wasser umkristallisiert.



  Process for the preparation of sulfanilic acid-3-aminoanilide. It has been found that anilides -der sulf-a.nilic acid from aromatic diamines have an excellent action against streptococci in vivo. Anilides of sulphanilic 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 subject of the present patent is a process for the preparation of sulfanilic acid-3-aminoanilide, which is characterized in that: an acylsulfanilic acid halide is allowed to act on a mono-acyl-meta-phenylenediamine and in the product obtained in this way . splits off the acyl groups.



  The sulfanilic acid .3-aminoanilide melts at 158 to <B> 160 '. </B> It is quite soluble in alcohol and methyl alcohol and easily dissolves in acids and alkalis. The new connection is intended to be used as a drug.



  <I> Example; </I> 40 parts of monoacetyl-m-phenylenediamine hydrochloride are mixed with the calculated amount of crude, moist acetylsulfanilic acid chloride in aqueous solution. The condensation is caused by the slow addition of dilute sodium hydroxide solution. The alkaline solution is filtered and the condensation product is precipitated from the addition of acid.

   The acetylsulfanilic acid 3-acetylaminoanilide is boiled with 2.50 parts of 15% hydrochloric acid to split off the acetyl groups. The solution of the hydrochloride is neutralized, the sulfanilic acid 3-aminoanilide which crystallizes out is filtered off with suction and recrystallized from water.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 8ulfanil- säure-3-aminoanilid, dadurch gekennzeich- net,.dass man ein Acylsulfanil.säurehalogenid auf ein Mono-acyl-meta-phenylendiamin ein wirken lässt und im so erhaltenen Produkt die Acylgruppen abspaltet. Das Sulfanilsäure-3-aminoanilid schmilzt bei 158 bis<B>160'.</B> Es iet ziemlich löslich in Alkohol und Methylalkohol und löst sich leicht in Säuren und Lauben. PATENT CLAIM: Process for the preparation of 8ulfanilic acid-3-aminoanilide, characterized in that an acylsulfanil acid halide is allowed to act on a mono-acyl-meta-phenylenediamine and the acyl groups are split off in the product thus obtained. The sulfanilic acid 3-aminoanilide melts at 158 to <B> 160 '. </B> It is quite soluble in alcohol and methyl alcohol and easily dissolves in acids and arbor. Die neue Ver bindung soll als Arzneimittel verwendet werden. The new connection is intended to be used as a drug.
CH194684D 1936-05-28 1936-05-28 Process for the preparation of sulfanilic acid-3-aminoanilide. CH194684A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH191673T 1936-05-28
CH194684T 1936-05-28

Publications (1)

Publication Number Publication Date
CH194684A true CH194684A (en) 1937-12-15

Family

ID=25722157

Family Applications (1)

Application Number Title Priority Date Filing Date
CH194684D CH194684A (en) 1936-05-28 1936-05-28 Process for the preparation of sulfanilic acid-3-aminoanilide.

Country Status (1)

Country Link
CH (1) CH194684A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001002350A2 (en) * 1999-06-30 2001-01-11 Bayer Aktiengesellschaft Novel amino sulfonamides and amido sulfonamides as antiviral agents

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001002350A2 (en) * 1999-06-30 2001-01-11 Bayer Aktiengesellschaft Novel amino sulfonamides and amido sulfonamides as antiviral agents
WO2001002350A3 (en) * 1999-06-30 2001-03-29 Bayer Ag Novel amino sulfonamides and amido sulfonamides as antiviral agents

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