CH253119A - Process for the preparation of a new benzenesulfonylguanidine. - Google Patents

Process for the preparation of a new benzenesulfonylguanidine.

Info

Publication number
CH253119A
CH253119A CH253119DA CH253119A CH 253119 A CH253119 A CH 253119A CH 253119D A CH253119D A CH 253119DA CH 253119 A CH253119 A CH 253119A
Authority
CH
Switzerland
Prior art keywords
new
benzenesulfonyl
benzenesulfonylguanidine
amino
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 CH253119A publication Critical patent/CH253119A/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

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

Description

  

  Verfahren zur Darstellung eines neuen     Benzolsulfonylguanidin       Gegenstand des vorliegenden Patentes  bildet ein Verfahren zur     Herstellung    eines  neuen     Benzolsulfonylguanidins,    welches da  durch gekennzeichnet ist, dass man     einen     S - substituierten p -     Amino    -     benzolsulfonyl-          pseudo-thioharnstoff    mit     Allylamin    um  setzt.  



  Das so gewonnene     p-Amino-benzolsul-          fonyl-allylguanidin    schmilzt bei     153-154,5 .     Die neue     Verbindung    soll therapeutische  Verwendung finden.  



  Die als Ausgangsstoffe verwendeten  S - substituierten p -     Amino    -     benzolsulfonyl-          pseudo-thioharnstoffe    können dadurch erhal  ten werden, dass man einen     S-substituierten          pseudo-Thioharnstoff    mit einem     Benzol-          sulfonsäurehalogenid    umsetzt, das in     p-Stel-          lung    einen durch Hydrolyse oder Reduktion  in eine     Aminogruppe        überführbaren        Substi-          tuenten    enthält,

   und die erhaltene Verbin  dung mit     hydrolysierenden    bzw. reduzieren  den Mitteln behandelt.-    <I>Beispiel:</I>    Man versetzt die     Lösung    von 37 Teilen       Äthyl-pseudo-thioharnstoff-hydrobromid        in.     75 Teilen     trockenem        Pyridin    in Portionen  mit 47 Teilen     p-Acetylamino-benzolsulfo-          ehlorid.    Unter     Selbsterwärmung    erhält man  eine Lösung, die     man    noch 1     Stunde    auf  dem kochenden Wasserbad erwärmt und  dann in Wasser eingiesst.

   Der dabei sieh aus  scheidende N -     [p    -     Acetylamino    - benzolsul-         fonyll    - S -     äthyl    -     pseudo    -     thioharnstoff    der  Formel  
EMI0001.0043     
         wird        abgenutscht    und mit Wasser     gewaschen.     Man     kann    ihn durch     Umkristallisieren    aus  Alkohol reinigen. F. 182 .  



  1 Teil     N-[p-Acetylamino-benzolsulfonyl]-          S-äthyl-pseudo-thioharnstoff    wird mit 2  Teilen 17 %     iger    Salzsäure erwärmt, bis Lö  sung eintritt. Dann verdünnt man mit 5  Teilen Wasser und     neutralisiert    mit verdünn  ter     Sodalös.ung,    wobei N-     [p-Amino-benzol-          sulfonyl]-S-äthyl-pseudo-thioharnstoff    kri  stallisiert ausfällt. Man kann durch     Um-          kristallisieren        aus        verdünntem    Alkohol rei  nigen. F. 159-160 .

   Er hat die Formel  
EMI0001.0060     
    2,6 Teile     p-Amino-benzolsulfonyl-S-äthyl-          ps-eudo-thioharns,toff    werden mit 9     Teilen          Allylamin    während 3     Stunden    am     Rückfluss     gekocht, wobei man     eine    Lösung erhält. Das  gebildete     Äthylmercaptan    wird mit dem  überschüssigen     Allylamin    auf dem Wasser  bad     abdestilliert    und der Rückstand mit  Wasser verrührt.

   Die erhaltene Kristallisa  tion von     p-Amino-benzolsulfonyl-allylguan-          idin    wird     abgenutscht,    mit Wasser gewaschen  und getrocknet.     Ausbeute    93 % der Theorie;  F. 153-154  (aus verdünntem Alkohol).



  Process for preparing a new benzenesulfonylguanidine The subject of the present patent is a process for the preparation of a new benzenesulfonylguanidine, which is characterized in that an S - substituted p - amino - benzenesulfonyl pseudo-thiourea is implemented with allylamine.



  The p-amino-benzenesulfonyl-allylguanidine obtained in this way melts at 153-154.5. The new compound should find therapeutic use.



  The S-substituted p-amino-benzenesulfonyl-pseudo-thioureas used as starting materials can be obtained by reacting an S-substituted pseudo-thiourea with a benzenesulfonic acid halide which, in the p-position, is produced by hydrolysis or reduction contains substituents which can be converted into an amino group,

   and the compound obtained is treated with hydrolyzing or reducing agents.- <I> Example: </I> The solution of 37 parts of ethyl pseudo-thiourea hydrobromide in 75 parts of dry pyridine is added in portions with 47 parts of p -Acetylamino-benzenesulfo-chloride. With self-heating a solution is obtained, which is warmed for 1 hour on a boiling water bath and then poured into water.

   The outgoing N - [p - acetylamino - benzenesulfonyl - S - ethyl - pseudo - thiourea of the formula
EMI0001.0043
         is sucked off and washed with water. It can be purified by recrystallizing it from alcohol. F. 182.



  1 part of N- [p-acetylamino-benzenesulfonyl] - S-ethyl-pseudo-thiourea is heated with 2 parts of 17% hydrochloric acid until solution occurs. Then it is diluted with 5 parts of water and neutralized with dilute soda solution, with N- [p-amino-benzenesulfonyl] -S-ethyl-pseudo-thiourea precipitating crystallized. It can be purified by recrystallization from dilute alcohol. F. 159-160.

   He has the formula
EMI0001.0060
    2.6 parts of p-amino-benzenesulfonyl-S-ethyl-ps-eudo-thiourine, toff are refluxed with 9 parts of allylamine for 3 hours, a solution being obtained. The ethyl mercaptan formed is distilled off with the excess allylamine on the water bath and the residue is stirred with water.

   The resulting crystallization of p-amino-benzenesulfonyl-allylguanidine is filtered off with suction, washed with water and dried. Yield 93% of theory; F. 153-154 (from dilute alcohol).

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Benzolsulfonylguanidins., dadurch gekenn- zeichnet, daB man einen S-substituierten p -Amino-benzolsulfonyl-pseudo-thioharnstoff mit Allylamin umsetzt. Das so gewonnene p-Amino-benzolsul- fonyl-allylguanidin schmilzt bei 153-154,5 . Die neue Verbindung soll therapeutische Verwendung finden. PATENT CLAIM: Process for the preparation of a new benzenesulfonylguanidine., Characterized in that an S-substituted p -amino-benzenesulfonyl-pseudo-thiourea is reacted with allylamine. The p-amino-benzenesulfonyl-allylguanidine obtained in this way melts at 153-154.5. The new compound should find therapeutic use.
CH253119D 1941-12-12 1941-12-12 Process for the preparation of a new benzenesulfonylguanidine. CH253119A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH253119T 1941-12-12

Publications (1)

Publication Number Publication Date
CH253119A true CH253119A (en) 1948-02-15

Family

ID=4469830

Family Applications (1)

Application Number Title Priority Date Filing Date
CH253119D CH253119A (en) 1941-12-12 1941-12-12 Process for the preparation of a new benzenesulfonylguanidine.

Country Status (1)

Country Link
CH (1) CH253119A (en)

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