CH259700A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259700A
CH259700A CH259700DA CH259700A CH 259700 A CH259700 A CH 259700A CH 259700D A CH259700D A CH 259700DA CH 259700 A CH259700 A CH 259700A
Authority
CH
Switzerland
Prior art keywords
preparation
chloro
biguanide derivative
bromophenyl
acid
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 CH259700A publication Critical patent/CH259700A/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     I4erstellung    von     Nl-3-Chlor-4-          brompheny1-N5-äthylbiguanid,    welches ein  wertvolles     ehemotherapeutisches    Mittel ist  oder als     Zwischenprodukt    für die Herstellung  von     cbeinotberapeutischen    Mitteln verwendet  werden kann. Es ist insbesondere ein wert  volles     Antimalariamittel.     



  Erfindungsgemäss wird die besagte neue  Verbindung, nämlich     N1-3-Chlor-4-brom-          phenyl-N5-ätliylbiguanid,    dadurch erhalten,  dass man     N'-Ätliyldicyandiamid    mit     3-Chlor-          4-bromanilin    umsetzt.  



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



  Das     Nl-3-Clilor-4-bromphenyl-N'-äthyl-          biguanid    stellt eine starke Base dar, welche  mit organischen und anorganischen Säuren       beständige    Salze ergibt, die in manchen Fäl  len 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 bequemer durch  Vermischen der Komponenten in einem orga  nischen Lösungsmittel, wie z. B.     Aeeton,    oder  in einem Alkohol, in     welchem    die Salze spär  lich löslich sind, hergestellt werden.

   Auf diese  Weise kann man beispielsweise die Salze mit    Essigsäure, Milchsäure,     Methansulfonsäure,          1lethylendisalicylsäure,        i@Iethylen-bis-f-oxy-          napht.hoesäure    und Salzsäure bequem her  stellen.  



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.         Beispiel:     Ein Gemisch von 11,2 Teilen     N3-Äthyl-          dicyandiainid    und 24,3 Teilen     3-Chlor-4-          l;i#omanilin-chlorhy        drat    in 75 Teilen     ss-Äthoxy-          ätlianol    wird während 3 Stunden unter Rück  fluss zum Sieden erhitzt. Hierauf lässt man  das Gemisch abkühlen, worauf     abfiltriert     wird.

   Der feste Rückstand wird mit kaltem       thylacetat    gewaschen und     aus    Wasser     inn-          kristallisiert.    Auf diese Weise erhält man     Nl-          3-Clilor-4-bromphenyl-N'-äthylbiguanid    in  Form seines     Monohydrochlorids,    welches bei  217  C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of Nl-3-chloro-4-bromophenyl-N5-ethylbiguanide, which is a valuable former therapeutic agent or can be used as an intermediate product for the preparation of non-therapeutic agents. It is a particularly valuable antimalarial drug.



  According to the invention, the said new compound, namely N1-3-chloro-4-bromophenyl-N5-ätliylbiguanid, is obtained by reacting N'-Ätliyldicyandiamid with 3-chloro-4-bromoaniline.



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



  The Nl-3-Clilor-4-bromophenyl-N'-ethyl biguanid is a strong base which, with organic and inorganic acids, gives stable salts which in some cases are easily soluble in water. The salts can be prepared by dissolving the base in aqueous solutions of the acid and then evaporating the water, but they can be more conveniently in dry form by mixing the components in an orga African solvent, such as. B. Aeeton, or in an alcohol in which the salts are sparse Lich soluble, are prepared.

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



  The following example serves to explain the invention. Example: A mixture of 11.2 parts of N3-ethyl dicyandiainide and 24.3 parts of 3-chloro-4-l; i # omaniline chlorohydrate in 75 parts of ß-ethoxy-ethanol is refluxed for 3 hours heated. The mixture is then allowed to cool and it is filtered off.

   The solid residue is washed with cold thylacetate and crystallized from water. In this way, Nl-3-chloro-4-bromophenyl-N'-ethyl biguanide is obtained in the form of its monohydrochloride, which melts at 217.degree.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Nl-3-Chlor- 4-bromphenyl-N'-äthylbiguanid, dadurch ge kennzeichnet, dass man N'-Ä thyldicyandiamid mit 3-Chlor-4-bromanilin umsetzt. Das NI-3-Chlor-4-broinphenyl-N'-äthyl- biguanid ist eine starke Base, deren Mono- hydrochlorid bei 217"C schmilzt. Die neue Base besitzt kräftige Antiinalariaeigenschaften. Claim: Process for the preparation of Nl-3-chloro-4-bromophenyl-N'-ethylbiguanide, characterized in that N'-Ä thyldicyandiamid is reacted with 3-chloro-4-bromoaniline. NI-3-chloro-4-broinphenyl-N'-ethyl biguanide is a strong base whose monohydrochloride melts at 217 "C. The new base has powerful anti-alarial properties.
CH259700D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259700A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259700X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259700A true CH259700A (en) 1949-01-31

Family

ID=27178056

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259700D CH259700A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259700A (en)

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