CH259708A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259708A
CH259708A CH259708DA CH259708A CH 259708 A CH259708 A CH 259708A CH 259708D A CH259708D A CH 259708DA CH 259708 A CH259708 A CH 259708A
Authority
CH
Switzerland
Prior art keywords
chloro
preparation
iodophenyl
biguanide derivative
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 CH259708A publication Critical patent/CH259708A/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     Nl-3-Chlor-4-          jodphenyl-N        '-ii-hropylbiguaiiid,    welches ein  wertvolles chemotherapeutisches Mittel ist oder  als Zwischenprodukt für die Herstellung von  chemotherapeutischen Mitteln     verwendet    wer  den kann. Es ist insbesondere ein wertvolle       Antimalariamittel.     



  Erfindungsgemäss wird die besagte neue  Verbindung, nämlich     Nl-3-Clilor-4-jodphenyl-          N'-n-propylbiguanid,    dadurch erhalten,     dal     man     N'-n-Propyldicyandiamid    mit     3-Chlor-4-          jodanilin    umsetzt.  



  Die Umsetzung erfolgt zweckmässig durch  Erhitzen eines Salzes des Amins mit dem  substituierten     Dicyandiamid    in     Cegenwart     eines Lösungsmittels, wie z. B. Wasser oder     ss-          Ätho.xyäthanol.     



  Das     NI        -3-Chlor-4-jodphenyl-N'-n-propyl-          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 sich dadurch herstellen, dass die Base       i,        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. Aceton, 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,          Nlethylendisalicylsäure,        llethylen-bis-ss-oxy-          iiaplithoesäure    und Salzsäure bequem her  stellen.  



  Das folgende Beispiel diene zur Erläute  rung der     Erfindung.       <I>Beispiel:</I>  Ein Gemisch von 12,6 Teilen     N3-n-Propyl-          dieyandiamid    und 32 Teilen     3-Chlor-4-          jodanilin-chlorhydrat    in 75 Teilen     ss-Ä        thoxy        -          äthanol    wird während 3 Stunden unter       Rückfluss    zum Sieden erhitzt. Hierauf lässt  man das Gemisch abkühlen, worauf     abfil-          triert    wird.

   Der feste Rückstand wird -mit  kaltem     Äthylacetat    gewaschen und aus Was  ser umkristallisiert. Auf diese Weise erhält  man     Nl-3-Chlor-4-jodphenyl-N'-n-propylbigua-          nid    in Form seines     Monohydrochlorids,    wel  ches bei 225  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-iodophenyl-N '-ii-hropylbiguaiiid, 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 Nl-3-chloro-4-iodophenyl-N'-n-propylbiguanide, is obtained by reacting N'-n-propyldicyandiamide with 3-chloro-4-iodaniline.



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



  The NI -3-chloro-4-iodophenyl-N'-n-propyl-biguanid 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 i, 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 orga African 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, methylenedisalicylic acid, ethylene-bis-β-oxyiaplithoic acid and hydrochloric acid can be conveniently prepared.



  The following example serves to explain the invention. <I> Example: </I> A mixture of 12.6 parts of N3-n-propyl-dieyandiamide and 32 parts of 3-chloro-4-iodaniline chlorohydrate in 75 parts of β-ethoxy ethanol is refluxed for 3 hours heated to boiling. The mixture is then allowed to cool, whereupon it is filtered off.

   The solid residue is washed with cold ethyl acetate and recrystallized from water. In this way, Nl-3-chloro-4-iodophenyl-N'-n-propylbiguanide is obtained in the form of its monohydrochloride, which melts at 225.degree.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N1-3-Chlor- 4-jodphenyl-N'-n-propylbiguanid, dadurch ge kennzeichnet, dass man N3-n-Propyldicyan- diamid mit 3-Chlor-4-jodanilin umsetzt. Das Ni - 3 - Chlor-4-jodphenyl-N'-n-propy 1- big-tianid ist eine starke Base, deren Mono hydrochlorid bei 225 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigensehaften. PATENT CLAIM: Process for the production of N1-3-chloro-4-iodophenyl-N'-n-propylbiguanide, characterized in that N3-n-propyldicyandiamide is reacted with 3-chloro-4-iodaniline. The Ni - 3 - chloro-4-iodophenyl-N'-n-propy 1-big-tianide is a strong base whose monohydrochloride melts at 225 ° C. The new base has strong anti-malarial properties.
CH259708D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259708A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259708X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259708A true CH259708A (en) 1949-01-31

Family

ID=27178064

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259708D CH259708A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259708A (en)

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