CH222175A - Process for preparing a cyclic sulfonic acid amide compound. - Google Patents

Process for preparing a cyclic sulfonic acid amide compound.

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Publication number
CH222175A
CH222175A CH222175DA CH222175A CH 222175 A CH222175 A CH 222175A CH 222175D A CH222175D A CH 222175DA CH 222175 A CH222175 A CH 222175A
Authority
CH
Switzerland
Prior art keywords
sulfonic acid
acid amide
amide compound
cyclic sulfonic
preparing
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH222175A publication Critical patent/CH222175A/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 einer     cyclisclien        Sulfonsäureamidverbinduv("g.       Wie im Hauptpatent Nr. 208085 angege  ben, ist, gelangt man zu gegen     Infektion,-          krankheiten    hoch wirksamen Verbindungen,  wenn man Abkömmlinge     cyclischer    Diamine       herstellt,    :die in den beiden ringständigen       Amino@gruppen        Benzols.ulfonylreste    tragen,  ,deren     p-Stellung    mit dem     Stickstoffatom     einer stickstoffhaltigen Gruppe verknüpft ist.  



  Gegenstand des vorliegenden     Patentes    ist  ein Verfahren zur Herstellung einer     cycli-          schen        Sulfonsäureamidverbindung,    welches  dadurch gekennzeichnet     ist,        dass    man ein       4.4'-Bis-(4"-aoylaminobenzolsulfonamido)-di-          phenylamin    zum     4.4'-Bs-(4"-aminobenzol-          sulfonamido)-diphenylamin    verseift.  



  Das so erhältliche neue Produkt wird  in schwach violetten,     kristallwasserhaltigen     Kristallen erhalten, die in Alkohol, Aceton  und Methanol     löslich    sind. Das. neue Produkt  soll in der Therapie Anwendung finden.    <I>Beispiel:

  </I>  4.4' - Bis - (4 "-     acetylaminoben!zolsulfon-          amido)-diphenylamin    (erhalten durch Um  setzung von 19,9 g     4.4'-Diaminodiphenyl-          amin    mit 47 g     4-Acetylaminobenzolsulfon-          säurechlorid    in 100     ein'        Pyridin,    schwach       violett    gefärbte     Kristallnadeln        aus-verdünn-          tem    Alkohol vom Schmelzpunkt     157-158'     unter Aufschäumen)

   wird durch     einstündiges     Kochen mit einer Mischung von gleichen  Raumteilen     konzentrierter    Natronlauge und  Wasser verseift. Dass aus der     Reaktions-          mischung    durch verdünnte Essigsäure aus  gefällte 4.4' -Bis - (4" -     aminobenzolsulfon-          amida)-diphenylamin    wird in schwach violet  ten, stark     kristallwasserhaltigen        Kria'tallen     gewonnen, die spielend leicht in Alkohol,  Aceton und Methanol löslich sind.



  Process for the preparation of a cyclic sulfonic acid amide compound ("g. As indicated in the main patent no. 208085, compounds that are highly effective against infection and diseases are obtained if derivatives of cyclic diamines are prepared: those in the two ring amino groups benzene Carry sulfonyl radicals, whose p-position is linked to the nitrogen atom of a nitrogen-containing group.



  The subject of the present patent is a process for the preparation of a cyclic sulfonic acid amide compound, which is characterized in that a 4,4'-bis (4 "-aoylaminobenzenesulfonamido) -diphenylamine is converted to 4,4'-Bs- (4" -aminobenzene- sulfonamido) -diphenylamine saponified.



  The new product thus obtainable is obtained in pale violet crystals containing water of crystallization, which are soluble in alcohol, acetone and methanol. The. new product should be used in therapy. <I> example:

  </I> 4.4 '- bis - (4 "- acetylaminobenzenesulfonamido) -diphenylamine (obtained by reacting 19.9 g of 4.4'-diaminodiphenylamine with 47 g of 4-acetylaminobenzenesulfonic acid chloride in 100 a' pyridine , pale violet colored crystal needles made of diluted alcohol with a melting point of 157-158 'with foaming)

   is saponified by boiling for one hour with a mixture of equal parts of the volume of concentrated sodium hydroxide solution and water. The 4.4'-bis (4 "- aminobenzenesulfonamide) -diphenylamine precipitated from the reaction mixture by dilute acetic acid is obtained in pale violet crystals which contain a lot of water of crystallization and which are easily soluble in alcohol, acetone and methanol .

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung einer cycli- schen Sulfonsäureamiclverbindung, dadurch gelkennzeiehnet, dass man ein 4.4'-Bis-(4"- acylaminobenzolsulfonamido) - diphenylamin zum 4.4'-Bis-(4"-aminobenzolsulfonamido)- diphenylamin verseift. Das so erhältliche neue Produkt wird in sehwach violetten, kristallwasserhaltigen Kristallen erhalten, die in Alkohol, Aceton und Methanol löslich sind. PATENT CLAIM: Process for the preparation of a cyclic sulfonic acid amicl compound, characterized in that a 4.4'-bis (4 "-acylaminobenzenesulfonamido) -diphenylamine is saponified to give 4.4'-bis- (4" -aminobenzenesulfonamido) -diphenylamine. The new product obtainable in this way is obtained in the form of weak violet crystals containing water of crystallization, which are soluble in alcohol, acetone and methanol.
CH222175D 1937-08-04 1938-07-14 Process for preparing a cyclic sulfonic acid amide compound. CH222175A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE222175X 1937-08-04
CH217886T 1938-07-14

Publications (1)

Publication Number Publication Date
CH222175A true CH222175A (en) 1942-06-30

Family

ID=25726083

Family Applications (1)

Application Number Title Priority Date Filing Date
CH222175D CH222175A (en) 1937-08-04 1938-07-14 Process for preparing a cyclic sulfonic acid amide compound.

Country Status (1)

Country Link
CH (1) CH222175A (en)

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