CH242495A - Process for the preparation of a new benzenesulfonamide derivative. - Google Patents

Process for the preparation of a new benzenesulfonamide derivative.

Info

Publication number
CH242495A
CH242495A CH242495DA CH242495A CH 242495 A CH242495 A CH 242495A CH 242495D A CH242495D A CH 242495DA CH 242495 A CH242495 A CH 242495A
Authority
CH
Switzerland
Prior art keywords
preparation
new
benzenesulfonamide derivative
amino
benzenesulfonamido
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 CH242495A publication Critical patent/CH242495A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Description

  

      Verfahren    zur Herstellung eines neuen     Benzolsulfonainidderivates.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines neuen       Benzolsulfonamidderivates,    das dadurch ge  kennzeichnet ist, dass man ein     2-Benzol-          sulfonamido    - 3,6 -     dimethyl    -     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    -     benzol-          sulfonamido.)    - 3,6 -     dimethyl    -     pyrazin    bildet  Kristalle vom     Schmelzpunkt    223-224 . Die  neue     Verbindung    soll als Arzneimittel sowie  als     Zwischenprodukt        Verwendung    finden.  



  Das 2 -     BenzolsuHonamido    - 3,6 -     dimethyl-          pyrazin,    das in     p-Stellung    zur     Sulfonamid-          gruppe        einen    durch Hydrolyse     in    die     Amino-          gruppe        überführbaren        Substituenten    enthält,  kann auf verschiedene Art und Weise ge  wonnen werden.

   Besonders geeignet ist die  Umsetzung der entsprechenden reaktions  fähigen     Benzolsulfonsäurederivate,    insbeson  dere der     Benzolsulfonsäurehalogenide,    mit         3,6-Dimethyl-pyrazinverbindungen,    die in       2-Stellung    eine Gruppe enthalten, die mit  dem     Benzolsulfonsäurederivat    ein     2-Benzol-          sulfonamido-3,6-dimethyl-pyrazin    zu bilden  vermag, wie mit 2     -Amino    - 3,6 -     dimethyl-          pyrazin.    Man     kann    auch entsprechende Sul  fonamide der Formel R .

       SOZNHY,    in der Y  einen bei der nachfolgenden     Reaktion    sich  abspaltenden Rest bedeutet, mit     2-Halogen-          3,6-dimethyl-pyrazinen    umsetzen. Auch kön  nen andere dem Fachmann geläufige     Her-          stellungsmethoden    benützt werden.    <I>Beispiel:</I>  123 Teile     2-Amino-3,6-dimethyl-pyrazin     werden in 400     Teilen    trockenem     Pyridin    ge  löst und unter Rühren mit 265,5 Teilen  p -     Carbäthogyamino    -     benzolsulfochlorid        in     kleinen Portionen versetzt.

   Man erwärmt  45     Minuten    lang auf 95 ,     destilliert    das       Pyridin    im Vakuum auf dem Wasserbad ab  und versetzt den noch warmen Rückstand  mit warmem Wasser. Man erhält Kristalle      des 2 - (p -     Carbäthoxyamino    -     benzolsulfon        -          amido)-3,6-dimethyl-pyrazins,    die nach dem  Erkalten     abgenutscht    und mit Wasser ge  waschen werden.  



  Der noch     feuchte        Nutschenkuchen        wird          in    1200 Teilen     2n-Natronlauge    1     Stunde    lang  auf dem kochenden Wasserbad     erwärmt,    mit  Tierkohle verrührt und nach dem Erkalten       filtriert.    Aus dem Filtrat fällt man durch  Neutralisieren mit Salzsäure das gebildete  2 - (p -     Amino    -     benzolsulfonamido)    - 3,6 -     di-          methyl-pyrazin    aus. Man kristallisiert     aus          heissem    Wasser um. F. 223-224 .  



  Es ist möglich,     die    Hydrolyse auch mit  andern alkalischen Mitteln, beispielsweise       Erdalkalihydroxyden,    wie     Calciumhydroxyd,     oder mit sauren Mitteln, z. B. Salzsäure, in       Gegenwart    von Wasser oder organischen Lö  sungsmitteln, wie Alkohol,     durchzuführen.       Das gebildete     p-Amino-benzolsulfönamid-          derivat        iässt    sich     ferner    in Form seiner Salze,       z-.    B. des     Natriums    oder des     Calciums,     isolieren.



      Process for the preparation of a new benzenesulfonainide derivative. The present patent relates to a process for the preparation of a new benzenesulfonamide derivative, which is characterized in that a 2-benzenesulfonamido - 3,6 - dimethyl - pyrazine which has a substituent which can be converted into the amino group by hydrolysis in the p-position , treated with a hydrolyzing agent.



  The 2 - (p - amino - benzenesulfonamido.) - 3,6 - dimethyl - pyrazine thus obtained forms crystals with a melting point of 223-224. The new compound is to be used as a drug and as an intermediate product.



  The 2-benzene-sulfonamido-3,6-dimethylpyrazine, 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 implementation of the corresponding reactive benzenesulfonic acid derivatives, in particular the benzenesulfonic acid halides, with 3,6-dimethylpyrazine compounds which contain a group in the 2-position which is a 2-benzene sulfonamido-3,6-dimethyl with the benzenesulfonic acid derivative is particularly suitable -pyrazine is able to form, as with 2-amino-3,6-dimethyl pyrazine. Corresponding sulphonamides of the formula R can also be used.

       SOZNHY, in which Y denotes a radical which is split off in the subsequent reaction, with 2-halo-3,6-dimethylpyrazines. Other production methods known to the person skilled in the art can also be used. <I> Example: </I> 123 parts of 2-amino-3,6-dimethyl-pyrazine are dissolved in 400 parts of dry pyridine and, while stirring, 265.5 parts of p-carbethogyamino-benzenesulfochloride are added in small portions.

   The mixture is heated to 95 for 45 minutes, the pyridine is distilled off in vacuo on a water bath, and warm water is added to the still warm residue. Crystals of 2 - (p - carbethoxyamino - benzenesulfone - amido) -3,6-dimethylpyrazine are obtained which, after cooling, are suction filtered and washed with water.



  The still moist nutsch cake is heated in 1200 parts of 2N sodium hydroxide solution for 1 hour on a boiling water bath, stirred with animal charcoal and, after cooling, filtered. The 2 - (p - amino - benzenesulfonamido) - 3,6 - dimethylpyrazine formed is precipitated from the filtrate by neutralization with hydrochloric acid. It is recrystallized from hot water. F. 223-224.



  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. B. hydrochloric acid, in the presence of water or organic solvents such as alcohol, to perform. The p-amino-benzenesulfonamide derivative formed 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 neuen Benzolsulfonamidderivates, dadurch gekenn zeichnet, daB man ein 2.-Benzolsulfonamido- 3,6 - dimethyl - pyrazin, das in p-Stellung einen durch Hydrolyse in die Aminogruppe überführbaren Substituenten aufweist, mit einem hydrolysierenden Mittel behandelt. PATENT CLAIM: Process for the preparation of a new benzenesulfonamide derivative, characterized in that a 2.-benzenesulfonamido 3,6-dimethylpyrazine, 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 - benzol- sulf onamido) - 3,6 - dimethyl - pyrazin bildet Kristalle vom Schmelzpunkt 223-224 . Die neue Verbindung soll- als Arzneimittel sowie als Zwischenprodukt Verwendung finden. The 2 - (p - amino - benzenesulfonamido) - 3,6 - dimethyl - pyrazine thus obtained forms crystals with a melting point of 223-224. The new compound should be used as a drug and as an intermediate product.
CH242495D 1939-05-23 1941-05-23 Process for the preparation of a new benzenesulfonamide derivative. CH242495A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE242495X 1939-05-23
CH240222T 1941-05-23

Publications (1)

Publication Number Publication Date
CH242495A true CH242495A (en) 1946-05-15

Family

ID=25728493

Family Applications (1)

Application Number Title Priority Date Filing Date
CH242495D CH242495A (en) 1939-05-23 1941-05-23 Process for the preparation of a new benzenesulfonamide derivative.

Country Status (1)

Country Link
CH (1) CH242495A (en)

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