CH250000A - Process for the preparation of a benzenesulfonamide derivative. - Google Patents

Process for the preparation of a benzenesulfonamide derivative.

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Publication number
CH250000A
CH250000A CH250000DA CH250000A CH 250000 A CH250000 A CH 250000A CH 250000D A CH250000D A CH 250000DA CH 250000 A CH250000 A CH 250000A
Authority
CH
Switzerland
Prior art keywords
preparation
amino
benzenesulfonamide derivative
benzenesulfonamido
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 CH250000A publication Critical patent/CH250000A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D237/00Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
    • C07D237/30Phthalazines

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

      Verfahren    zur Herstellung eines     Benzolsulfonamidderivates.       Gegenstand des vorliegenden Patentes ist       c-in    Verfahren zur Herstellung des im       seli@reiz.    Patent Nr. ?42490     beschriebenen          Benzolsulfonamidderivates,    das dadurch     ge-          i:ennzeiehnet    ist, dass man ein     1-Benzolsulfon-          ;;

  mido-phtalaziii,    das im     Benzolring    in       li-Stellung    zur     SulfonamidgTuppe    einen durch  Reduktion in die     Aminogruppe        überführ-          1> < iren        Substituenten    aufweist, mit einem re  duzierenden Mittel behandelt.  



  Das     1-Benzolsulfonamido-phtalazin,    das  im     Benzolring    in     p-Stellung    zur     Sulfon-          ainidgruppe    einen durch     Reduktion    in die       Aininogruppe        überführbaren        Substituenten     enthält, kann auf verschiedene Art und  Weise gewonnen werden.

   Besonders geeignet  ist die Umsetzung der entsprechenden reak  tionsfähigen     Benzolsulfonsäurederivate,    ins  besondere der     Benzolsulfonsäurehalogenide,     mit     Phtalazinverbindungen,    die in     1-Stellung     eine Gruppe enthalten, die mit dem Benzol  sulfonsäurederivat ein     1-Benzolsulfonamido-          phtalazin    zu bilden vermag,     insbesondere     mit 1 -     Amino    -     phtala.zin.    Man kann aber  a     uch    entsprechende Sulfonamide der Formel       l1.SO:

  ,NHY,    in der Y     einen    bei der Reaktion  sich abspaltenden Rest bedeutet, mit     1-Ha-          logen-phtalazinen    umsetzen oder andere dem       Fachmann    geläufige     Flerstellungsmethoden     benutzen. .  



       Beispiel        r:     28,4 g 1 - (p -     Nitro    -     benzolsulfonamido)-          hhIalazin,    das durch Kondensation von     p-Ni-          ti,o-benzolsulfo(,liiorid    mit     1-Amino-phtalazin          nrha.lten    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     )Vasserstoffaufnahme     bei 100-120  behandelt. Nach dem Erkalten       jvird    vom Katalysator     abfiltriert    und die     al-          hoholisehe    Lösung eingedampft.

   Dabei fällt  das gebildete 1-(p     Amino-benzolsulfonamido)-          plitalazin    kristallin an. Die Verbindung kann  zur Reinigung aus verdünntem Alkohol,     (ye-          gebenenfalls    unter Zusatz von Tierkohle,  umkristallisiert werden. Schmelzpunkt 241 .       Beispiel   <I>2:</I>  28,4 g     1-(p--Nitro-benzolsulfonamido)-          phtalazin    werden     mittels    67,7 g     Zinnchlorür     (Hydrat) und der doppelten Gewichtsmenge       konzentrierter    Salzsäure reduziert.

   Das ge  bildete 1 - (p -     Amino    -     benzolsulfonamido)-          phtalazin    wird isoliert und gegebenenfalls  umkristallisiert. Schmelzpunkt 241 .  



  Das entstandene     p-Amino-benzolsulfon-          amidderiva,t        lä.sst    sieh auch in Form     seiner     Salze, z. B. des Natriums oder des Kalziums,  isolieren.



      Process for the preparation of a benzenesulfonamide derivative. The subject of the present patent is c-in process for the production of the im seli @ Reiz. Benzene sulfonamide derivative described in U.S. Patent No. 42490, which is designated as being a 1-benzenesulfone ;;

  mido-phthalaziii, which has a substituent in the benzene ring in the 1-position to the sulfonamide group, which has been converted into the amino group by reduction, is treated with a reducing agent.



  The 1-benzenesulfonamido-phthalazine, which contains a substituent which can be converted into the amino group by reduction in the benzene ring in the p-position to the sulfonamine group, can be obtained in various ways.

   The reaction of the corresponding reactive benzenesulfonic acid derivatives, in particular the benzenesulfonic acid halides, with phthalazine compounds which contain a group in the 1-position which is able to form a 1-benzenesulfonamido-phtalazine with the benzene sulfonic acid derivative, in particular with 1-amino-phthalazine, is particularly suitable .zin. However, one can also use corresponding sulfonamides of the formula l1.SO:

  , NHY, in which Y denotes a radical which is split off during the reaction, react with 1-halophthalazines or use other preparation methods familiar to the person skilled in the art. .



       Example r: 28.4 g of 1 - (p - nitro - benzenesulfonamido) - halazine, which was obtained by condensation of p-Ni, o-benzenesulfo (, liioride with 1-amino-phthalazine,

   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 end of the) hydrogen uptake at 100-120. After cooling, the catalyst is filtered off and the alcoholic solution is evaporated.

   The 1- (p-amino-benzenesulfonamido) - plitalazine formed is obtained in crystalline form. For purification, the compound can be recrystallized from dilute alcohol (ye- if necessary with the addition of animal charcoal. Melting point 241. Example 2: 28.4 g of 1- (p-nitro-benzenesulfonamido) -phthalazine are reduced using 67.7 g of tin chloride (hydrate) and twice the amount by weight of concentrated hydrochloric acid.

   The 1 - (p - amino - benzenesulfonamido) - phtalazine formed is isolated and, if necessary, recrystallized. Melting point 241.



  The resulting p-amino-benzenesulfonamide derivative, t lä.sst also see in the form of its salts, e.g. B. of sodium or calcium, isolate.

 

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Herstellung eines Ben7ol- sulfonamiclderivates, dadurch gekennzeich net, dass man ein 1-Benzoisulfonamido- lilitalazin, das im Benzolring in p-Stellung zur Sulfonamidgruppe einen durch Reduk tion in die Aminogruppe überführbaren Substituenten aufweist, mit einem reduzie renden Mittel behandelt. <B> PATENT CLAIM: </B> Process for the preparation of a ben7ol sulfonamicl derivative, characterized in that a 1-benzoisulfonamido lilitalazine 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, treated with a reducing agent.
CH250000D 1939-05-23 1941-05-23 Process for the preparation of a benzenesulfonamide derivative. CH250000A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE250000X 1939-05-23
CH244345T 1941-05-23

Publications (1)

Publication Number Publication Date
CH250000A true CH250000A (en) 1947-07-31

Family

ID=25728928

Family Applications (1)

Application Number Title Priority Date Filing Date
CH250000D CH250000A (en) 1939-05-23 1941-05-23 Process for the preparation of a benzenesulfonamide derivative.

Country Status (1)

Country Link
CH (1) CH250000A (en)

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