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CH244509A - Process for the preparation of a new benzenesulfonamide derivative. - Google Patents

Process for the preparation of a new benzenesulfonamide derivative.

Info

Publication number
CH244509A
CH244509A CH244509DA CH244509A CH 244509 A CH244509 A CH 244509A CH 244509D A CH244509D A CH 244509DA CH 244509 A CH244509 A CH 244509A
Authority
CH
Switzerland
Prior art keywords
preparation
methyl
new
amino
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 CH244509A publication Critical patent/CH244509A/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-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
    • C07D241/20—Nitrogen atoms
    • C07D241/22—Benzenesulfonamido pyrazines

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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 neuen     Benzolsulfonamidderivates.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines neuen       Benzolsulfonamidderivai@es,    das dadurch ge  kennzeichnet ist, dass man ein     2-Benzolsulfon-          amida-6-methyl-pyrazin,    das in     p-Stellung     einen durch Hydrolyse in die     Aminogruppe          überführbaren        Substituenten        aufweist,    mit  einem     hydrolysierenden    Mittel behandelt.  



  Das so erhaltene     2-(p-Amino-benzolsulfon-          amido)-6-methyl-pyrazin    bildet Kristalle vom       Schmelzpunkt    258-260 . Die neue Verbin  dung soll als     Arzneimittel    sowie als.     Zwischen-          produkt        Verwendung        finden.     



  Das     2.-Benzolsulfonamido-6-methyl-pyr-          azin,    das in     p-Stellung    zur     Sulfonamidgruppe          einen    durch Hydrolyse in die     Aminogruppe          überführbaren        Substituenten    enthält, kann  auf verschiedene Art und Weise gewonnen  werden.

   Besonders geeignet ist die Umsetzung  der     entsprechenden    reaktionsfähigen     Benzol-          sulfonsäurederivate,    insbesondere der     Benzol-          sulfonsäurehalogenide,    mit     6-Methyl-pyrazin-          verbindungen,    die in     2-Stellung    eine     Gruppe       enthalten, die mit dem     Benzolsulfonsäure-          derivat    ein     2-Benzolsulfonamidomethylpyr-          a-zin    zu bilden vermag,

       wie    mit     2-Amino-6-          methyl-pyrazin.    Man kann auch     entspre-          ,nde    Sulfonamide der Formel R .     S02NHY,     <B>c</B>     'he     in der Y einen bei nachfolgender     Real,,tion     sich abspaltenden Rest bedeutet, mit     2-Halo-          gen    - 6     @        methyl;-        pyrazinen        umsetzen.    Auch  können andere dem Fachmann geläufige Her  stellungsmethoden benutzt werden.

      <I>Beispiel:</I>    109     Teile    2 -     Amino    - 6     -methyl    -     pyrazin     (F. 95-113"; erhalten durch Einwirkung  von     2,4,5-Triamino-_6-oxjT-pyrimidin        auf        Me-          thylglyoxal,

          Aufspaltung    des     Pyrimidinrin-          ges        mittels    Natronlauge und     Decarboxylie-          rung    der 2 -     Amino    -     methylpyra.zin    -     carbon-          säure)    werden in 400     Teilen    trockenem     Pyr-          idin    gelöst und     untrer    Rühren mit 265,

  5 Teilen       p    -     Carbäthoxyamino    -     benzolsulfochlorid    in  kleinen Portionen versetzt. Man erwärmt 60  Minuten lang auf 95",     destilliert    das über-           schüssige        Py        ridin    im Vakuum auf dem Was  serbad ab und versetzt den noch warmen       Rücli:stand    mit. warmem Wasser.

   Man erhält       Kristalle.    des     2-(p-Carbiithoxyamino-benzol-          sulfonamido)    - 6 -     methyl    -     pyrazins,    die nach  dem Erkalten     abgenutscht    und mit Wasser  gewaschen werden. Man kann aus 50 %     igem     Alkohol     umkristallisieren.     



  100 Teile vom     Nutschenkuchen    werden in  400 Teilen     2n-Natronlau-.e    1 Stunde lang auf  dem kochenden Wasserbad erwärmt, mit.  Tierkohle verrührt und nach dem Erkalten  filtriert. Aus dem Filtrat fällt man durch  Neutralisation mit Salzsäure das gebildete  ?'-     (p-Aminb-benzolsulfonamido)    -     6i-        methyl-          pyrazin    aus. Man kristallisiert aus 50 %     igem     Alkohol um. F.     258-260 .     



  Es     ist    möglich, die Hydrolyse auch mit  andern alkalischen Mitteln,     beispielsweise          Erdalkalihydroxyden,    wie     Calciumhydroxyd,     oder mit sauren Mitteln, z.     $.    Salzsäure, in    Gegenwart     von    Wasser oder organischen  Lösungsmitteln, wie Alkohol, durchzuführen.  



  Das gebildete     p-Aminobenzolsulfonamid-          clerivat    lässt     sich    ferner in     Form    seiner Salze,  z. B. des Natriums oder des     Calciums,    isolie  ren.



      Process for the preparation of a new benzenesulfonamide derivative. The subject of the present patent is a process for the preparation of a new benzenesulfonamide derivative, which is characterized in that a 2-benzenesulfonamide-6-methylpyrazine which has a substituent in the p-position which can be converted into the amino group by hydrolysis , treated with a hydrolyzing agent.



  The 2- (p-amino-benzenesulfonamido) -6-methyl-pyrazine thus obtained forms crystals with a melting point of 258-260. The new connec tion is intended as a drug as well as. Find intermediate product use.



  The 2.-benzenesulfonamido-6-methyl-pyrazine, which contains a substituent which can be converted into the amino group by hydrolysis in the p-position to the sulfonamide group, can be obtained in various ways.

   The reaction of the corresponding reactive benzenesulfonic acid derivatives, in particular the benzenesulfonic acid halides, with 6-methylpyrazine compounds which contain a group in the 2-position which, with the benzenesulfonic acid derivative, form a 2-benzenesulfonamidomethylpyr-a-zin, is particularly suitable able to form

       as with 2-amino-6-methyl-pyrazine. Corresponding sulfonamides of the formula R can also be used. S02NHY, <B> c </B> 'he in which Y denotes a residue which is split off in the subsequent realization, with 2-halogen - 6 @ methyl; - react pyrazines. Other production methods familiar to those skilled in the art can also be used.

      <I> Example: </I> 109 parts of 2-amino-6-methyl-pyrazine (F. 95-113 "; obtained by the action of 2,4,5-triamino-6-oxyT-pyrimidine on methylglyoxal,

          Splitting of the pyrimidine ring by means of sodium hydroxide solution and decarboxylation of the 2-amino-methylpyrazine-carboxylic acid) are dissolved in 400 parts of dry pyridine and, with stirring, with 265,

  5 parts of p-carbethoxyamino-benzenesulfochloride are added in small portions. The mixture is heated to 95 ″ for 60 minutes, the excess pyridine is distilled off in vacuo on the water bath, and warm water is added to the warm water.

   Crystals are obtained. des 2- (p-Carbiithoxyamino-benzenesulfonamido) - 6 - methyl - pyrazines, which are sucked off after cooling and washed with water. You can recrystallize from 50% alcohol.



  100 parts of the Nutsche cake are heated in 400 parts of 2N sodium bicarbonate .e for 1 hour on the boiling water bath, with. Mix animal charcoal and filter after cooling. The? '- (p-amine-b-benzenesulfonamido) -6imethylpyrazine formed is precipitated from the filtrate by neutralization with hydrochloric acid. It is recrystallized from 50% alcohol. F. 258-260.



  It is possible to carry out the hydrolysis with other alkaline agents, for example alkaline earth metal hydroxides such as calcium hydroxide, or with acidic agents, e.g. $. Hydrochloric acid, in the presence of water or organic solvents such as alcohol.



  The p-aminobenzene sulfonamide derivative formed can also be used in the form of its salts, e.g. B. of sodium or calcium, isolie ren.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen lienzolsulfonamidderivates, dadurch gekenn zeichnet, dass man ein ?-Benzolsulfonamido-6- methyl-py razin, das in p-Stellung einen durch Hydrolyse in die Aminogruppe überführ baren Substituenten aufweist, mit einem hydrolysierenden Mittel behandelt. PATENT CLAIM: A process for the preparation of a new lienzolsulfonamide derivative, characterized in that a? -Benzolsulfonamido-6-methyl-py razine, which has a substituent which can be converted into the amino group by hydrolysis, is treated with a hydrolyzing agent. Das so erhaltene 2-(p-Amino-benzolsulfon- amido)-6-methyl-pyra.zin bildet Kristalle vom Schmelzpunkt 258-2(_t0". Die neue Verbin dung soll als Arzneimittel sowie als Zwischen produkt Verwendung finden. The 2- (p-amino-benzenesulfonamido) -6-methyl-pyrazine obtained in this way forms crystals with a melting point of 258-2 (_t0 "). The new compound is intended to be used as a drug and as an intermediate product.
CH244509D 1939-05-23 1941-05-23 Process for the preparation of a new benzenesulfonamide derivative. CH244509A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE244509X 1939-05-23
CH240222T 1941-05-23

Publications (1)

Publication Number Publication Date
CH244509A true CH244509A (en) 1946-09-15

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Family Applications (1)

Application Number Title Priority Date Filing Date
CH244509D CH244509A (en) 1939-05-23 1941-05-23 Process for the preparation of a new benzenesulfonamide derivative.

Country Status (1)

Country Link
CH (1) CH244509A (en)

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