CH259661A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259661A
CH259661A CH259661DA CH259661A CH 259661 A CH259661 A CH 259661A CH 259661D A CH259661D A CH 259661DA CH 259661 A CH259661 A CH 259661A
Authority
CH
Switzerland
Prior art keywords
preparation
diiodophenyl
biguanide derivative
acid
ethylbiguanide
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 CH259661A publication Critical patent/CH259661A/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     N1-3,4-Dijod-          plienyl-N'-ätliylbiguanid,    welches ein wert  volles chemotherapeutisches Mittel ist oder  als Zwischenprodukt für die Herstellung von  chemotherapeutischen Mitteln verwendet wer  den kann. Es ist insbesondere ein wertvolles       Antimalariamittel.     



  Erfindungsgemäss wird die besagte neue  Verbindung, nämlich     N1-3,4-Dijodphenyl-N'-          ü.tliylbiguanid,    dadurch erhalten, dass man       N'-Ätliyldicyandiamid    mit     3,4-Dijodanilin     umsetzt.  



  Die Umsetzung erfolgt zweckmässig durch  Erhitzen eines Salzes des Amins mit dem       substituierten        Dic@jandiamid    in Gegenwart  eines Lösungsmittels, wie z. B. Wasser oder       ss-Ä        tlioxyäthanol.     



  Das     N'-3,4-Dijodphenyl-N'-äthylbiguanid     stellt eine starke Base dar, welche mit orga  nischen und anorganischen Säuren beständige  Salze ergibt, die in manchen Fällen in Wasser  leicht löslich sind. Die Salze lassen sich da  durch 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     organischen    Lö  sungsmittel, wie z. B. Aceton, oder in einem  Alkohol, in welchem die Salze spärlich löslich    sind, hergestellt werden.

   Auf diese Weise  kann man beispielsweise die     Salze    mit Essig  säure, Milchsäure,     Methansulfonsäure,        Me-          thylendisalicy        lsäure,        Methylen-bis-ss-oxynaph-          thoesäure    und Salzsäure bequem herstellen.  



  Das folgende Beispiel diene zur Erläute  rung der     Erfindung.     



  <I>Beispiel:</I>  Ein Gemisch von 11,2 Teilen     N3-Äthyl-          dicy        andiamid    und 38,2 Teilen     3,4-Dijodani-          lin-chlorhydrat    in 125 Teilen     ss-Äthoxyäthanoi     wird während 3 Stunden unter     Rückfluss     zum Sieden erhitzt. Hierauf lässt man das Ge  misch abkühlen, worauf     abfiltriert    wird. Der  feste Rückstand wird mit kaltem     Äthy        laeetat     gewaschen und aus Wasser unikristallisiert.

    Auf diese Weise erhält man     N1-3,4-Dijod-          phenyl    - N' -     äthylbiguanid    in Form seines       3vIonohydrochlorids,    welches bei 212-213  C  schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of N1-3,4-diiodoplienyl-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-diiodophenyl-N'- ü.tliylbiguanid, is obtained by reacting N'-Ätliyldicyandiamid with 3,4-diiodaniline.



  The reaction is conveniently carried out by heating a salt of the amine with the substituted Dic @ jandiamid in the presence of a solvent, such as. B. water or ss-Ä tlioxyäthanol.



  The N'-3,4-diiodophenyl-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 produced by dissolving the base in aqueous solutions of the acid and then evaporating the water, but they can be in dry form. more convenient by mixing the components in an organic solvent such. B. acetone, or in an alcohol in which the salts are sparingly soluble.

   In this way, for example, the salts with acetic acid, lactic acid, methanesulfonic acid, methylenedisalicylic 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 N3-ethyl dicyandiamide and 38.2 parts of 3,4-diiodaniline chlorohydrate in 125 parts of ß-ethoxyethanoi is refluxed for 3 hours heated. The mixture is then allowed to cool, whereupon it is filtered off. The solid residue is washed with cold ethyl acetate and unicrystallized from water.

    In this way, N1-3,4-diiodophenyl - N '- ethyl biguanide is obtained in the form of its 3vionohydrochloride, which melts at 212-213 ° C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N1-3,4-Di- jodphenyl-N'-äthylbiguanid, dadurch gekenn zeichnet, dass man N3-Äthyldicyandiamid mit 3,4-Dijodanilin umsetzt. Das N1-3,4-Dijodphenyl-N'-äthylbiguanid ist eine starke Base, deren Monohydroehlorid bei 212-213 C schmilzt. Die neue Base be sitzt kräftige Antimalariaeigenschaften. PATENT CLAIM: Process for the production of N1-3,4-diiodophenyl-N'-ethylbiguanide, characterized in that N3-ethyldicyandiamide is reacted with 3,4-diiodaniline. The N1-3,4-diiodophenyl-N'-ethylbiguanide is a strong base whose monohydrochloride melts at 212-213 ° C. The new base has powerful anti-malarial properties.
CH259661D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259661A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259661X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259661A true CH259661A (en) 1949-01-31

Family

ID=27178017

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259661D CH259661A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259661A (en)

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