CH259676A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259676A
CH259676A CH259676DA CH259676A CH 259676 A CH259676 A CH 259676A CH 259676D A CH259676D A CH 259676DA CH 259676 A CH259676 A CH 259676A
Authority
CH
Switzerland
Prior art keywords
preparation
methyl
bromophenyl
biguanide derivative
propylbiguanide
Prior art date
Application number
Other languages
German (de)
Inventor
Limited Imperial Ch Industries
Original Assignee
Ici Ltd
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 Ici Ltd filed Critical Ici Ltd
Publication of CH259676A publication Critical patent/CH259676A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
    • C07C279/24—Y being a hetero atom
    • C07C279/26—X and Y being nitrogen atoms, i.e. biguanides

Landscapes

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

Description

  

  Verfahren zur Herstellung eines     Biguanidderivates.       Die vorliegende Erfindung betrifft ein  Verfahren zur Herstellung von     N'-p-Brom-          phenyl-N'-methyl-N'-n-propylbig-uanid,    wel  ches ein wertvolles chemotherapeutisches  Mittel ist oder als Zwischenprodukt für die  Herstellung von     chemotherapeutischen    Mit  teln     verwendet    werden kann. Es ist insbeson  dere ein wertvolles     Antimalariamittel.     



  Erfindungsgemäss wird die besagte neue  Verbindung, nämlich     N'-p-Bromphenyl-N'-          methyl-N'-n-propylbiguanid,    dadurch erhal  ten, dass man     N'-Methyl-N3-n-propyldicyan-          diamid    mit     p-B'roma.nilin    umsetzt.  



  Die     Umsetzung    erfolgt zweckmässig durch  Erhitzen eines     Salzes    des Amins mit dem       substituierten        Dicya.ndiamid    in     Gegenwart     eines Lösungsmittels, wie z. B. Wasser oder       l-Äthoxyäthanol.     



       Das.        N'        -,p-Bromphenyl-N'-met.hyl-N'-n-          propylbiguanid    stellt eine starke Base dar,  welche mit organischen und anorganischen  Säuren     beständige    Salze ergibt, die in man  chen Fällen in Wasser leicht löslich sind.  Die Salze lassen sieh dadurch     herstellen,    dass  die     Base    in     wässrigen        Lösungen    der Säure  gelöst und hierauf das Wasser verdampft  wird, doch können sie in trockener     Form    be  quemer durch Vermischen der Komponenten  in einem organischen     Lösungsmittel,    wie z. B.

         Aceton,        oder    in einem Alkohol, in welchem  die Salze spärlich löslich sind,     hergestellt     werden. Auf diese Weise kann man beispiels  weise die Salze mit Essigsäure, Milchsäure,         Methansulfonsäure,        iblethylendisalicylsäure,          1Vlethylen-bis-l-oxynaphthoesäure    und Salz  säure bequem herstellen.  



  Das folgende Beispiel diene zur     Erläu-          terung    der Erfindung.  



       Beispiel:     Ein Gemisch von 14 Teilen     N3-Methyl-          N3-,n-propyldicyandiamid    und 20,8 Teilen       p-Bromanilin-chlorhydrat    in 60     Teilen    ss  Äthoxyäthanol     wird    während 3 Stunden un  ter     Rückfluss    zum Sieden: erhitzt. Hierauf  lässt man das Gemisch abkühlen, worauf ab  filtriert wird.

   Der feste Rückstand wird mit  kaltem Äther gewaschen und aus Wasser       umkristallisiert.    Auf     diese    Weise erhält man       N'-    p -     Bromphenyl-N'-methyl-N'-        n-propylbi-          guanid    in Form seines     Monohydrochlorids,     welches bei 251  C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of N'-p-bromophenyl-N'-methyl-N'-n-propylbig-uanid, wel Ches is a valuable chemotherapeutic agent or used as an intermediate for the preparation of chemotherapeutic agents can be. It is especially a valuable antimalarial agent.



  According to the invention, said new compound, namely N'-p-bromophenyl-N'-methyl-N'-n-propylbiguanide, obtained by adding N'-methyl-N3-n-propyldicyandiamide with p-B ' roma.nilin implements.



  The reaction is conveniently carried out by heating a salt of the amine with the substituted Dicya.ndiamid in the presence of a solvent, such as. B. water or l-ethoxyethanol.



       The. N '-, p-bromophenyl-N'-meth.hyl-N'-n-propylbiguanide is a strong base which, with organic and inorganic acids, results in stable salts which in some cases are easily soluble in water. The salts can be prepared in that the base is dissolved in aqueous solutions of the acid and then the water is evaporated, but they can be quemer in dry form by mixing the components in an organic solvent, such as. B.

         Acetone, or in an alcohol in which the salts are sparingly soluble. In this way, for example, the salts with acetic acid, lactic acid, methanesulfonic acid, iblethylene disalicylic acid, 1Vlethylene-bis-1-oxynaphthoic acid and hydrochloric acid can be conveniently prepared.



  The following example serves to explain the invention.



       Example: A mixture of 14 parts of N3-methyl-N3-, n-propyldicyandiamide and 20.8 parts of p-bromaniline chlorohydrate in 60 parts of ss ethoxyethanol is heated to the boil for 3 hours under reflux. The mixture is then allowed to cool, whereupon it is filtered off.

   The solid residue is washed with cold ether and recrystallized from water. In this way, N'- p - bromophenyl-N'-methyl-N'- n-propylbiguanide is obtained in the form of its monohydrochloride, which melts at 251.degree.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N'-p-Brom- phenyl-N'-methyl-N'-n-propylbiguanid, da durch gekennzeichnet, dass man N3-Methyl- N3-n-propyldicyandiamid mit p-Bromanilin umsetzt. Das Nl-p-Bromphenyl-N'-methyl-N'-n- propylbiguanid ist eine starke Base, deren Monohydrochlorid bei 251 C schmilzt. Die neue Base besitzt, kräftige Antimalariaeigen- schaften. PATENT CLAIM: A process for the production of N'-p-bromophenyl-N'-methyl-N'-n-propylbiguanide, characterized in that N3-methyl-N3-n-propyldicyandiamide is reacted with p-bromoaniline. Nl-p-bromophenyl-N'-methyl-N'-n-propylbiguanide is a strong base, the monohydrochloride of which melts at 251.degree. The new base has strong antimalarial properties.
CH259676D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259676A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259676X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259676A true CH259676A (en) 1949-01-31

Family

ID=27178032

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259676D CH259676A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259676A (en)

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