CH250003A - Process for the preparation of a benzenesulfonamide derivative. - Google Patents

Process for the preparation of a benzenesulfonamide derivative.

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Publication number
CH250003A
CH250003A CH250003DA CH250003A CH 250003 A CH250003 A CH 250003A CH 250003D A CH250003D A CH 250003DA CH 250003 A CH250003 A CH 250003A
Authority
CH
Switzerland
Prior art keywords
pyridazine
methyl
benzenesulfonamido
preparation
benzenesulfonamide derivative
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH250003A publication Critical patent/CH250003A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/20—Nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

  

  <B>Verfahren zur Herstellung eines</B>     Benzolsulfonamidderivates.            Gegenstand    des vorliegenden Patentes     ist     ein     Verfahren    zur     Herstellung    des im       ehweiz.    Patent Nr.

   242493 beschriebenen       Benzolsulfonamidderivates,    das dadurch     ge-          kennzeichnet        ist,    dass man ein     3-Benzolsul-          fonamido-6-m,ethyl-pyridazin,    das im     Benzol-          ring    in     p-Stellung    zur     Sulfonamidgruppe     einen durch Reduktion in die     Aminogruppe          überführbaren        Substituenten    aufweist, mit  einem reduzierenden Mittel behandelt.  



  Das 3 -     Benzols,ulfonamido    - 6 -     methyl-          pyridazin,    das im     Benzolring    in     p-Stellung     zur     Sulfonamidgruppe    einen durch Reduk  tion in die     Aminogruppe        überführbaren        Sub-          stituenten    enthält, kann auf verschiedene  Art und Weise gewonnen werden.

       Besonders          geeignet        ist    die Umsetzung der entsprechen  den reaktionsfähigen     Benzolsulfonsäurederi-          vate,        insbesondere    der     Benzolsulfonsäure-          halogenide,    mit     6-Methyl-pyridazinverbin-          dungen,    die in     3-Stellung        eine    Gruppe ent  halten,

   die mit dem     Benzolsulfonsäure-          derivat    ein     3-Benzolsulfonamido-6-methyl-          pyridazin    zu bilden vermag, insbesondere  mit     3-Amino-6-methyl-pyridazin.    Man kann  aber auch     entsprechende        Sulfonamide    der  Formel     RS02NHY,    in der Y einen bei der  Reaktion sich abspaltenden Rest     bedeutet,     mit     3-Halogen-6-methyl-pyridazinen    um  setzen oder andere dem Fachmann geläufige  Herstellungsmethoden benutzen.

      <I>Beispiel 1:</I>  29,4 g     3-(p-Nitro-benzolsulfonamido)-6-          methyl-pyridazin,    das durch     Kondensation     von p -     Nitro    -     benzolsulfochlorid    mit aus       3-Chlor-6-methyl-pyridazin    und Ammoniak       gewonnenem    3 -     Amino    - 6 -     methyl    -     pyridazin     erhalten wurde,

   werden in der 50fachen  Menge absolutem Alkohol gelöst und mit  10     Gewichtsprozenten    eines     Nickel-Träger-          Katalysators        im        Rührautoklaven    mit Wasser  stoff     unter        einem    Überdruck von 50     Atm        bis     zur Beendigung der     Wasserstoffaufnahme     bei 100-120  behandelt. Nach dem Erkal  ten wird vom     Katalysator        abfiltriert    und die  alkoholische Lösung eingedampft.

   Dabei fällt  das gebildete     3-(p-Amino-benzolsulfonamido)-          6-methyl-pyridazin    kristallin an. Die Ver  bindung kann zur Reinigung aus     verdünntem     Alkohol, gegebenenfalls unter     Zusatz    von  Tierkohle,     umkristallisiert    werden.     Schmelz-          punkt    190-191 .

           Beispiel   <I>2:</I>  29,4 g     3-(p-N'itro-benzolsulfonamido)-6-          methyl-pyridazin    werden     mittels    67,7 g       Zinnehlorür    (Hydrat) und .der doppelten Ge  wichtsmenge konzentrierter Salzsäure     redu-          ziert.    Das     gebildete        3-(p-Amino-benzolsulfon-          amido)-6-methyl-py        ridazin    wird     isoliert    und  gegebenenfalls umkristallisiert. Schmelz  punkt 190-191 .

        Das     entstandene        p-Amino-benzolsulfon-          amidderivat    lässt sich auch in Form     seine     Salze, z. B.     des    Natriums oder des Kalziums,  isolieren.



  <B> Process for the production of </B> a benzenesulfonamide derivative. The subject of the present patent is a process for the production of the in ehweiz. Patent no.

   242493 described benzenesulfonamide derivative, which is characterized in that a 3-benzenesulfonamido-6-m, ethyl-pyridazine, which has a substituent which can be converted into the amino group by reduction in the benzene ring in the p-position to the sulfonamide group, with treated with a reducing agent.



  The 3 - benzene, sulfonamido - 6 - methylpyridazine, which in the benzene ring in the p-position to the sulfonamide group contains a substituent which can be converted into the amino group by reduction, can be obtained in various ways.

       The reaction of the corresponding reactive benzenesulfonic acid derivatives, in particular the benzenesulfonic acid halides, with 6-methyl-pyridazine compounds which contain a group in the 3-position is particularly suitable,

   which is able to form a 3-benzenesulfonamido-6-methyl-pyridazine with the benzenesulfonic acid derivative, in particular with 3-amino-6-methyl-pyridazine. However, corresponding sulfonamides of the formula RS02NHY, in which Y is a radical which is split off during the reaction, can also be reacted with 3-halo-6-methyl-pyridazines or other preparation methods familiar to the person skilled in the art can be used.

      <I> Example 1: </I> 29.4 g of 3- (p-nitro-benzenesulfonamido) -6-methyl-pyridazine, which is obtained by condensation of p-nitro-benzenesulfonyl chloride with 3-chloro-6-methyl-pyridazine 3 - amino - 6 - methyl - pyridazine obtained from ammonia and obtained,

   are dissolved in 50 times the amount of absolute alcohol and treated with 10 percent by weight of a nickel-supported catalyst in a stirred autoclave with hydrogen under a pressure of 50 atm until the hydrogen uptake ceases at 100-120. After cooling, the catalyst is filtered off and the alcoholic solution is evaporated.

   The 3- (p-amino-benzenesulfonamido) - 6-methyl-pyridazine formed is obtained in crystalline form. For cleaning, the compound can be recrystallized from dilute alcohol, optionally with the addition of animal charcoal. Melting point 190-191.

           Example <I> 2: </I> 29.4 g of 3- (p-nitro-benzenesulfonamido) -6-methyl-pyridazine are reduced by means of 67.7 g of tin chloride (hydrate) and twice the amount by weight of concentrated hydrochloric acid - adorns. The 3- (p-amino-benzenesulfonamido) -6-methyl-pyridazine formed is isolated and, if necessary, recrystallized. Melting point 190-191.

        The resulting p-amino-benzenesulfonamide derivative can also be used in the form of its salts, e.g. B. of sodium or calcium, isolate.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Benzol- sulfonamidderivates, dadurch gekennzeieh- net, dass man ein 3-Benzolsulfonamido-6- methyl-pyridazin, das im Benzolring in p-Stellung zur Sulfonamidgruppe:einen durch Reduktion in die Aminogruppe überführ baren Substituenten aufweist, mit einem reduzierenden Mittel behandelt. PATENT CLAIM: Process for the production of a benzene sulfonamide derivative, characterized in that a 3-benzenesulfonamido-6-methyl-pyridazine, which in the benzene ring in the p-position to the sulfonamide group has a substituent which can be converted into the amino group by reduction, with treated with a reducing agent.
CH250003D 1939-05-23 1941-05-23 Process for the preparation of a benzenesulfonamide derivative. CH250003A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE250003X 1939-05-23
CH244346T 1941-05-23

Publications (1)

Publication Number Publication Date
CH250003A true CH250003A (en) 1947-07-31

Family

ID=25728931

Family Applications (1)

Application Number Title Priority Date Filing Date
CH250003D CH250003A (en) 1939-05-23 1941-05-23 Process for the preparation of a benzenesulfonamide derivative.

Country Status (1)

Country Link
CH (1) CH250003A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1018423B (en) * 1954-11-10 1957-10-31 American Cyanamid Co Process for the preparation of 3-sulfanilamido-6-substituted pyridazines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1018423B (en) * 1954-11-10 1957-10-31 American Cyanamid Co Process for the preparation of 3-sulfanilamido-6-substituted pyridazines

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