CH240580A - Process for the preparation of p-amino-benzenesulfonylguanidine. - Google Patents

Process for the preparation of p-amino-benzenesulfonylguanidine.

Info

Publication number
CH240580A
CH240580A CH240580DA CH240580A CH 240580 A CH240580 A CH 240580A CH 240580D A CH240580D A CH 240580DA CH 240580 A CH240580 A CH 240580A
Authority
CH
Switzerland
Prior art keywords
amino
benzenesulfonylguanidine
pseudo
thiourea
preparation
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 CH240580A publication Critical patent/CH240580A/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
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/64—X and Y being nitrogen atoms, e.g. N-sulfonylguanidine

Landscapes

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

Description

  

  Verfahren zur Herstellung von     p-Ämino-benzolsulfonylguanidin.       Gegenstand des vorliegenden     Patentes     bildet ein Verfahren zur Herstellung von       p-Amino-benzolsulfonylguanidin,    das dadurch  gekennzeichnet     ist,        daB    man einen     S-substi-          tuierten        Benzolsulfonyl-pseudo-thioharnstoff,     dessen     Benzolkern    in     p-Stellung    einen durch  Hydrolyse in die     Aminogruppe    überführ  baren     Substituenten    enthält,

   mit Ammoniak  umsetzt und die erhaltene Verbindung mit       hydrolysierenden        Mitteln    behandelt.  



  Das so gewonnene     p-Amino-benzolsul-          fonylguanidin    ist bekannt und soll therapeu  tische Verwendung finden.  



  Die als     Ausgangsstoffe    verwendeten     Thio-          harnstoffe    lassen sich leicht durch Konden  sation der entsprechend     p-substituierten        Ben-          zolsulfonsäurehalogenide    mit     S-substituierten          Pseudo-thioharnstoffen        bezw.    ihren Salzen in       Pyridin    herstellen.  



  <I>Beispiel:</I>  30     Teile        N-(p-Acetylamino-benzolsulfo-          nyl)-S-äthyl-pseudo-thioharnstoff    vom     F.182      (dargestellt durch Kondensation von S-Äthyl-         pseudo-thioharnstoff-hydrobromid    mit     p-Ace-          tylaminobenzol-sulfochlorid    in     Pyridin)    wer  den mit 200 Teilen     verdünnter    Ammoniak  lösung gekocht, wobei     Merkaptan        entweicht.     Man erhält     eine    klare Lösung,

   aus der sich  beim Abkühlen     p-Acetylamino-benzolsulfo-          nylguanidin    kristallisiert abscheidet. Es ist  mit einer geringen Menge     p-Amino-benzol-          sulfonylguanidin    vermengt, welches durch  eine teilweise     Verseifung    durch die ver  dünnte     Ammoniaklösung    entstanden ist.  



  1 Teil des erhaltenen Produktes     wird    mit  2 Teilen 17 %     iger    Salzsäure bis zur vollstän  digen Lösung erwärmt, mit 3 Teilen Wasser  verdünnt, mit Tierkohle entfärbt und filtriert.  Nun     wird        mit    Natronlauge das     p-Amino-ben-          zolsulfonylguanidin    kristallin gefällt und  aus Wasser umkristallisiert.     F.187,5-189,5 .     



  Als Ausgangsstoff kann man statt     p-Acetyl-          amino    -     benzolsulfonyl    - S -     äthyl        -pseudo-thio-          harnstoff    auch     p-Acetylamino-benzolsul-          fonyl-S-benzyl-pseudo-thioharnstoff    verwen  den, der leicht durch     Kondensation    von       S-Benzyl        -pseudo-thioharnstoff-hydrochlorid         mit p -     Acetylamino    -     benzolsulfochlorid    in       Pyridin    erhalten wird.



  Process for the preparation of p-aminobenzenesulfonylguanidine. The present patent relates to a process for the preparation of p-amino-benzenesulfonylguanidine, which is characterized in that an S-substituted benzenesulfonyl-pseudo-thiourea whose benzene nucleus is in the p-position has a substituent which can be converted into the amino group by hydrolysis contains,

   reacted with ammonia and treated the compound obtained with hydrolyzing agents.



  The p-amino-benzenesulfonylguanidine obtained in this way is known and is intended to be used in therapy.



  The thioureas used as starting materials can be easily bezw by condensation of the corresponding p-substituted benzene sulfonic acid halides with S-substituted pseudo-thioureas. make their salts in pyridine.



  <I> Example: </I> 30 parts of N- (p-acetylamino-benzenesulfonyl) -S-ethyl-pseudo-thiourea from F.182 (produced by condensation of S-ethyl pseudo-thiourea hydrobromide with p Acetylaminobenzene sulfochloride in pyridine) who boiled with 200 parts of dilute ammonia solution, whereby mercaptan escapes. A clear solution is obtained

   from which p-acetylamino-benzenesulfonylguanidine is precipitated in crystallized form on cooling. It is mixed with a small amount of p-aminobenzenesulfonylguanidine, which is the result of partial saponification by the diluted ammonia solution.



  1 part of the product obtained is heated with 2 parts of 17% hydrochloric acid to a complete solution, diluted with 3 parts of water, decolorized with animal charcoal and filtered. The p-amino-benzenesulfonylguanidine is then precipitated in crystalline form with sodium hydroxide solution and recrystallized from water. F.187.5-189.5.



  Instead of p-acetylamino-benzenesulfonyl-S-ethyl-pseudo-thiourea, p-acetylamino-benzenesulfonyl-S-benzyl-pseudo-thiourea can be used as the starting material, which is easily produced by condensation of S-benzyl - pseudo-thiourea hydrochloride with p - acetylamino - benzenesulfochloride in pyridine is obtained.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von p-Amino- benzolsulfonylguanidin, dadurch gekenn zeichnet, dass man einen S-substituierten Ben- zolsulfonyl-pseudo-thioharnstoff, dessen Ben- zolkern in p-Stellung einen durch Hydrolyse in die Aminogruppe überführbaren Substi- tuenten enthält, PATENT CLAIM: A process for the production of p-Amino-benzenesulfonylguanidine, characterized in that an S-substituted benzenesulfonyl-pseudo-thiourea whose benzene nucleus in the p-position contains a substituent which can be converted into the amino group by hydrolysis, mit Ammoniak umsetzt und die erhaltene Verbindung mit hydrolysieren- den Mitteln behandelt. <B>UNTERANSPRUCH:</B> Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man N-(p-Acetylamino- i5 benzolsulf onyl) - S-äthyl-pseudo-thioharnstof f als Ausgangsstoff verwendet. reacted with ammonia and treated the compound obtained with hydrolyzing agents. SUBCLAIM: Process according to patent claim, characterized in that N- (p-acetylamino- i5 benzenesulfonyl) - S-ethyl-pseudo-thiourea is used as the starting material.
CH240580D 1941-12-16 1941-12-16 Process for the preparation of p-amino-benzenesulfonylguanidine. CH240580A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH240580T 1941-12-16
CH236130T 1941-12-16

Publications (1)

Publication Number Publication Date
CH240580A true CH240580A (en) 1945-12-31

Family

ID=25728066

Family Applications (1)

Application Number Title Priority Date Filing Date
CH240580D CH240580A (en) 1941-12-16 1941-12-16 Process for the preparation of p-amino-benzenesulfonylguanidine.

Country Status (1)

Country Link
CH (1) CH240580A (en)

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