CH259713A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259713A
CH259713A CH259713DA CH259713A CH 259713 A CH259713 A CH 259713A CH 259713D A CH259713D A CH 259713DA CH 259713 A CH259713 A CH 259713A
Authority
CH
Switzerland
Prior art keywords
preparation
bromo
iodophenyl
biguanide derivative
water
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 CH259713A publication Critical patent/CH259713A/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     Nl-3-Brom-          4-jodphenyl-N'-ä.thylbiguanid,    welches ein  wertvolles 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     Nl-3-Brom-4-jodphenyl-          N'-äthylbiguanid,    dadurch erhalten, dass  man     N'-Äthyldicyandiamid    mit     3-Brom-4-jod-          anilin    umsetzt.  



  Die Umsetzung erfolgt zweckmässig durch  Erhitzen eines Salzes des Amins mit dem sub  stituierten     Dicyandiamid    in Gegenwart eines  Lösungsmittels, wie z. B. Wasser oder       Äthoxyäthanol.     



  Das     NI-3-Brom-4-jodphenyl-NS-äthylbigua-          nid    stellt eine starke Base dar, welche mit  organischen und anorganischen Säuren be  ständige Salze ergibt, die in manchen Fällen  in Wasser leicht löslich sind. Die Salze lassen  sich dadurch herstellen, dass die Base in     wäss-          rigen    Lösungen der Säure gelöst und hierauf  das Wasser verdampft wird, doch können sie  in trockener Form bequemer durch Ver  mischen der Komponenten in einem organi  schen Lösungsmittel, wie z. B. Aceton, oder  in einem Alkohol, in welchem die Salze spär  lich löslich sind, hergestellt werden.

   Auf diese    Weise kann man beispielsweise die Salze     mii     Essigsäure, Milchsäure,     Methansulfonsäure,          l@lethylendisalicylsäure,        Methylen-bis-ss-oxy-          naphthoesäure    und Salzsäure bequem her  stellen.  



  Das folgende Beispiel diene     zur    Erläute  rung der Erfindung.  



  <I>Beispiel:</I>  Ein Gemisch von 11,2 Teilen     N'-Äthyl-          dicyandiamid    und 23,4 Teilen     3-Brom-4-jod-          anilin-chlorhYdrat    in 40 Teilen Wasser wird  während 3 Stunden unter     Rückfluss    zum Sie  den erhitzt. Hierauf lässt man das     Gemisch.     abkühlen, worauf     abfiltriert    wird. Der feste  Rückstand wird mit kaltem Wasser gewaschen  und aus Wasser umkristallisiert.

   Auf diese       'f4Teise    erhält man     Nl-3-Brom-4-jodphenyl-N'-          äthylbiguanid    in Form seines     Monohydro-          chlorids,    welches bei 220 bis 221 C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of Nl-3-bromo-4-iodophenyl-N'-a.thylbiguanide which is a valuable chemotherapeutic agent or which can be used as an intermediate for the preparation of chemotherapeutic agents. In particular, it's a valuable .. full antimalarial drug.



  According to the invention, said new compound, namely Nl-3-bromo-4-iodophenyl-N'-ethylbiguanide, is obtained by reacting N'-ethyldicyandiamide with 3-bromo-4-iodo-aniline.



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



  The NI-3-bromo-4-iodophenyl-NS-äthylbigua- nid 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 alcohol in which the salts are sparse Lich soluble, are produced.

   In this way, for example, the salts with acetic acid, lactic acid, methanesulfonic acid, ethylenedisalicylic acid, methylene-bis-β-oxynaphthoic acid and hydrochloric acid can be conveniently prepared.



  The following example serves to explain the invention.



  <I> Example: </I> A mixture of 11.2 parts of N'-ethyl dicyandiamide and 23.4 parts of 3-bromo-4-iodo-aniline chlorohydrate in 40 parts of water is refluxed for 3 hours heated. Then leave the mixture. cool, whereupon it is filtered off. The solid residue is washed with cold water and recrystallized from water.

   In this way, Nl-3-bromo-4-iodophenyl-N'-ethyl biguanide is obtained in the form of its monohydrochloride, which melts at 220 to 221.degree.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Nl-3-Brom- 4-jodphenyl-NJ-ä.thylbiguanid, dadurch ge kennzeichnet, dass man N3-Äthyldicyandiamicl mit 3-Brom-4-jodanilin umsetzt. Das Nl-3-Brom-4-jodphenyl-N'-äthylbigua- nid ist eine starke Base, deren Monohydro- chlorid bei 220 bis 221 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigenschaften. PATENT CLAIM: Process for the preparation of Nl-3-bromo-4-iodophenyl-NJ-ä.thylbiguanid, characterized in that N3-ethyldicyandiamicl is reacted with 3-bromo-4-iodaniline. The Nl-3-bromo-4-iodophenyl-N'-ethylbiguanide is a strong base whose monohydrochloride melts at 220 to 221.degree. The new base has powerful anti-malarial properties.
CH259713D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259713A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259713X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259713A true CH259713A (en) 1949-01-31

Family

ID=27178069

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259713D CH259713A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259713A (en)

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