CH259695A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259695A
CH259695A CH259695DA CH259695A CH 259695 A CH259695 A CH 259695A CH 259695D A CH259695D A CH 259695DA CH 259695 A CH259695 A CH 259695A
Authority
CH
Switzerland
Prior art keywords
preparation
biguanide derivative
acid
dibromophenyl
salts
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 CH259695A publication Critical patent/CH259695A/en

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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     N1-3,4-Di-          brompheii-,-1-N        ,-ätliylbiguanid,    welches ein        -erteolles    chemotherapeutisches Mittel ist  oder als Zwischenprodukt für die Herstellung  von chemotherapeutischen Mitteln     verwendet     werden kann. Es ist insbesondere ein wert  volles     Antimalariamittel.     



  Erfindungsgemäss wird die besagte neue  Verbindung, nämlich     N1-3,4-Dibromphenyl-N'-          äthylbiguanid,    dadurch erhalten, dass man     N-'-          ÄthyIdieyandiamid    mit     3,4-Dibromanilin    um  setzt.  



  Die Umsetzung erfolgt. zweckmässig durch  Erhitzen eines Salzes des Amins mit dein sub  stituierten     Dieyandiamid    in Gegenwart eines  Lösungsmittels, wie z. B. Wasser oder       Äthoxyätlianol.     



  Das     N'-3,4-Dibromphenyl-N'-äthylbiguanid     stellt eine starke Base dar, welche mit organi  schen und anorganischen Säuren beständige  Salze ergibt, die in manchen Fällen in Wasser  leicht löslich sind. Die Salze lassen sich dadurch  herstellen, dass die Base in     wässrigen    Lösun  gen der Säure gelöst und hierauf das Wasser       verdampft    wird, doch können sie in trockener       Form        bequemer    durch Vermischen der Kom  ponenten in einem organischen Lösungs  mittel, wie z. B. Aceton, oder in einem Al  kohol, in welchem die Salze spärlich löslich  sind, hergestellt werden.

   Auf diese Weise    kann man beispielsweise die Salze     finit    Essig  Milchsäure,     llethansulfonsäure,        lle-          s        'iure,          t.liylendisalicylsäure,        llethylen-bis-f-oxynaph-          thoesäure    und Salzsäure bequem herstellen.  Das folgende Beispiel diene     zur    Erläute  rung der Erfindung.

           Beispiel:     Ein Gemisch von 1.1,2 Teilen     Ns-Äthyl-          dicyandiamid    und 28,8 Teilen     3,4-Dibrom-          anilin-chlorhydrat    in 80 Teilen     fl'-Äthoxy-          äthanolwird    während 3 Stunden     unter    Rück  fluss zum Sieden erhitzt. Hierauf lässt man  das Gemisch abkühlen, worauf     abfiltriert     wird. Der feste Rückstand wird mit kaltem       Äthylacetat    gewaschen und aus Wasser um  kristallisiert.

   Auf diese Weise erhält man     Nl-          1,4-Dibromphenyl-N'-äth3-lbiguanid    in Form  <B>2</B>  seines     hlonohy        drochlorids,    welches bei 213  bis     \314     C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of N1-3,4-di-bromopheii -, - 1-N, -ätliylbiguanid, which is a valuable chemotherapeutic agent or can be used as an intermediate for the preparation of chemotherapeutic agents. It is a particularly valuable antimalarial drug.



  According to the invention, said new compound, namely N1-3,4-dibromophenyl-N'-ethylbiguanide, is obtained by reacting N -'-EthyIdieyandiamid with 3,4-dibromaniline.



  The implementation takes place. expediently by heating a salt of the amine with your sub-substituted Dieyandiamid in the presence of a solvent, such as. B. water or Äthoxyätlianol.



  The N'-3,4-dibromophenyl-N'-ethylbiguanide 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 more convenient in dry form by mixing the components in an organic solvent, such as. B. acetone, or in an Al alcohol in which the salts are sparingly soluble, are produced.

   In this way, for example, the salts finite acetic acid, lactic acid, ethanesulfonic acid, llesis, tert-liylenedisalicylic acid, ethylene-bis-f-oxynaphthoic acid and hydrochloric acid can be conveniently prepared. The following example serves to explain the invention.

           Example: A mixture of 1.1.2 parts of Ns-ethyl dicyandiamide and 28.8 parts of 3,4-dibromo aniline chlorohydrate in 80 parts of fl'-ethoxy ethanol is heated to boiling under reflux for 3 hours. The mixture is then allowed to cool and it is filtered off. The solid residue is washed with cold ethyl acetate and recrystallized from water.

   In this way, Nl-1,4-dibromophenyl-N'-eth3-lbiguanide is obtained in the form of its halohydrochloride, which melts at 213 to 314.degree.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N1-3,4-Di- bromphenyl-N'-äthylbiguanid, dadurch ge kennzeichnet, dass man N3-Äthyldicyandiamid mit 3,4-Dibromanilin umsetzt. Das N 1-3,4-Dibrompheny 1-N'-ätliy lbiguanicl ist eine starke Base, deren Monohydroehlorid bei 213 bis 214 C schmilzt. Die neue Base besitzt kräftige Antiinalariaeigenschaften. PATENT CLAIM: Process for the preparation of N1-3,4-dibromophenyl-N'-ethylbiguanide, characterized in that N3-ethyldicyandiamide is reacted with 3,4-dibromaniline. The N 1-3,4-dibromopheny 1-N'-ätliy Ibiguanicl is a strong base, the monohydrochloride melts at 213 to 214 C. The new base has strong anti-alarial properties.
CH259695D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259695A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259695X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259695A true CH259695A (en) 1949-01-31

Family

ID=27178051

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259695D CH259695A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259695A (en)

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