CH259684A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259684A
CH259684A CH259684DA CH259684A CH 259684 A CH259684 A CH 259684A CH 259684D A CH259684D A CH 259684DA CH 259684 A CH259684 A CH 259684A
Authority
CH
Switzerland
Prior art keywords
preparation
chloro
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 CH259684A publication Critical patent/CH259684A/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-4-Chlor-3-          jodphenyl-NF-isopropylbigtianid,    welches ein  wertvolles chemotherapeutisches     -Mittel    ist  oder als Zwischenprodukt für die Herstel  lung von chemotherapeutischen     -Mitteln    ver  wendet werden kann. Es ist insbesondere  ein wertvolles     Antimalariamittel.     



  Erfindungsgemäss wird die besagte neue  Verbindung, nämlich     Nl-4-Chlor-3-jodplienyl-          N'-isopropyIbigttanid,        dadurch    erhalten, dass  man     N'-Isopropyldicy        andiamid    mit     4-Chlor-3-          jodanilin    umsetzt.  



  Die     Unisetzung    erfolgt zweckmässig durch  Erhitzen eines Salzes des Amins mit dein  substituierten     Dicyandiamid    in Gegenwart  eines Lösungsmittels, wie z. B. Wasser oder       ss--@tliolyäthanol.     



  Das     Nl-4-Clilor-3-jodphenyl-N        >-isoliropyl-          biguanid    stellt eine starke Base dar, welche       reit    organischen und     anorganischen    Säuren  beständige Salze ergibt, die in manchen Fäl  len in Wasser leicht löslich sind.

   Die Salze       lassen    sich dadurch herstellen,     da-ss    die Base  in     wässrigen        Lösungen    der Säure gelöst und  hierauf das Wasser verdampft wird,     doch     können sie     iii    trockener     Forin    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,     hlethan-          sulfonsäure,        Metliylendisalicylsäure,        Methylen-          bis-,B-ox--iiaphthoesäure    Lind Salzsäure     bequem     herstellen. Das folgende Beispiel diene zur  Erläuterung der Erfindung.

      <I>Beispiel:</I>  Ein Gemisch von<B>12,6</B> Teilen     N'-Isopropyl-          dicyandiamid    und 30 Teilen     4-Chlor-3-jod-          anilin-chlorhydrat    in 90 Teilen     ss-Ätlioyy-          äthanol    wird während 3 Stunden unter       R,ückfluss        zum    Sieden     erhitzt.    Hierauf lässt  man das Gemisch abkühlen, worauf     abfiltriert     wird. Der feste Rückstand wird mit kaltem       t;thylacetat    gewaschen und aus Wasser um  kristallisiert.

   Auf diese Weise erhält man     N1-          q-Chlor-3-jodphenyl-N'-isopropi-lbiguanid    in  Form seines     iIonoliyclrochlorids,    welches bei  <B><U>938'</U></B> C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of Nl-4-chloro-3-iodophenyl-NF-isopropylbigtianide, which is a valuable chemotherapeutic agent or can be used as an intermediate for the manufacture of chemotherapeutic agents. It is a particularly valuable antimalarial drug.



  According to the invention, said new compound, namely Nl-4-chloro-3-iodoplienyl-N'-isopropylbigttanide, is obtained by reacting N'-isopropyldicyandiamide with 4-chloro-3-iodaniline.



  It is conveniently carried out by heating a salt of the amine with your substituted dicyandiamide in the presence of a solvent, such as. B. water or ss - @ tliolyäthanol.



  The Nl-4-Clilor-3-iodophenyl-N> -isoliropyl- biguanid is a strong base which gives stable salts with organic and inorganic acids, 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 dried more conveniently by mixing the components in an organic solvent, such as. B. acetone, or in an alcohol in which the salts are sparse Lich soluble, made. will.

   In this way, for example, the salts with acetic acid, lactic acid, ethanesulphonic acid, methylenedisalicylic acid, methylene bis-, B-ox- iaphthoic acid and hydrochloric acid can be conveniently prepared. The following example serves to illustrate the invention.

      <I> Example: </I> A mixture of <B> 12.6 </B> parts of N'-isopropyl dicyandiamide and 30 parts of 4-chloro-3-iodo-aniline chlorohydrate in 90 parts of ss-Ätlioyy- Ethanol is heated to the boil for 3 hours under reflux. The mixture is then allowed to cool and it is filtered off. The solid residue is washed with cold t; thylacetate and recrystallized from water.

   In this way, N1-q-chloro-3-iodophenyl-N'-isopropi-lbiguanide is obtained in the form of its iIonoliyclrochlorids, which melts at <B><U>938'</U> </B> C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N'-4-Chlor- 3-jodphenyl - N"- isopropylbiguanid, dadurch -gekennzeichnet, dass man N'-Isopropyldieyan- diamid mit 4-Clilor-3-jodanilin umsetzt. Das NI-4-Chlor-3-jodphenyl-N'-isopropyl- bigua.nid ist eine starke Base, deren -lono- hydrochlorid bei 238 C schmilzt. PATENT CLAIM: Process for the production of N'-4-chloro-3-iodophenyl - N "- isopropyl biguanide, characterized in that N'-isopropyldiyaniamide is reacted with 4-chloro-3-iodaniline. The NI-4-chlorine -3-iodophenyl-N'-isopropyl-bigua.nid is a strong base, the -lono hydrochloride of which melts at 238 C. Die neue Base besitzt. kräftige Antimalariaeimenschaften. The new base owns. powerful antimalarial properties.
CH259684D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259684A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259684X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259684A true CH259684A (en) 1949-01-31

Family

ID=27178040

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259684D CH259684A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259684A (en)

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