CH259703A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259703A
CH259703A CH259703DA CH259703A CH 259703 A CH259703 A CH 259703A CH 259703D A CH259703D A CH 259703DA CH 259703 A CH259703 A CH 259703A
Authority
CH
Switzerland
Prior art keywords
bromo
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 CH259703A publication Critical patent/CH259703A/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

  

  <B>Verfahren zur Herstellung</B>     eines        Biguanidderivates.       Die vorliegende Erfindung betrifft ein  Verfahren zur Herstellung von     Nl-4-Brom-3-          jodphenyl-N'-isopropylbiguanid,    welches ein  wertvolles     ehemotherapeutisehes    Mittel ist  oder als     Zwischenprodukt    für die Herstellung  von     chemotherapeutisehen    Mitteln verwendet  werden kann. Es ist insbesondere ein wert  volles     Antimalariamittel.     



  Erfindungsgemäss wird die besagte neue  Verbindung, nämlich     N1-4-Brom-3-jodphenyl-          N'-isopropylbiguanid,    dadurch erhalten, dass  man     N'-Isopropyldicyandiamid    mit     4-Brom-3-          jodanilin    umsetzt.  



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



  Das     Nl-4-Brom-3-jodphenyl-N'-isopropyl-          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       iti        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    Lösungsmittel, 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 Essigsäure, Milchsäure,     Methansulfon-          säure,        Methylendisalicylsäure,        Methylen-bis-ss-          oxynaphthoesäure    und Salzsäure bequem her  stellen.  



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.  



       Beispiel:     Ein     Gemisch    von 12,6 Teilen     N3-Isopropyl-          dicyandiamid    und 33,4 Teilen     4-Brom-3-jod-          anilin-chlorhydrat    in<B>100</B> Teilen     ss-Äthoxy-          äthanol         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  Ä     thylacetat    gewaschen und     aus    Wasser um  kristallisiert.

   Auf diese Weise erhält man     N'-          4-Brom-3-jodphenyl-N'-isopropylbiguanid    in  Form seines     Monohy        drochlorids,    welches bei  239  C schmilzt.



  <B> Process for the production </B> of a biguanide derivative. The present invention relates to a process for the preparation of Nl-4-bromo-3-iodophenyl-N'-isopropyl biguanide, which is a valuable post-therapeutic 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 N1-4-bromo-3-iodophenyl-N'-isopropylbiguanide, is obtained by reacting N'-isopropyldicyandiamide with 4-bromo-3-iodoaniline.



  The L implementation 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 ss- ethoxyethanol.



  The Nl-4-bromo-3-iodophenyl-N'-isopropyl biguanide 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 by dissolving the base in aqueous solutions of the acid and then evaporating the water. is, but they can be more conveniently in dry form by mixing the components in an organic solvent, such as. 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-s-oxynaphthoic acid and hydrochloric acid can be conveniently prepared.



  The following example serves to explain the invention.



       Example: A mixture of 12.6 parts of N3-isopropyl dicyandiamide and 33.4 parts of 4-bromo-3-iodo-aniline chlorohydrate in 100 parts of β-ethoxy ethanol is added for 3 hours Reflux heated to boiling. The mixture is then allowed to cool and it is filtered off. The solid residue is washed with cold ethyl acetate and crystallized from water.

   In this way, N'-4-bromo-3-iodophenyl-N'-isopropylbiguanide is obtained in the form of its monohydrochloride, which melts at 239.degree.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von NI-4-Brom- 3-joclphenyl-N'-isopropylbiguanid, dadurch gekennzeichnet, dass man N3-Isoprop@Tldicyan- diamid mit 4-Brom-3-jodanilin umsetzt. Das N'-4-Brom-3-jodphenyl-N'-isopropyl- biguanid ist eine starke Base, deren Mono- hydrochlorid bei 239 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigenschaften. PATENT CLAIM: A process for the preparation of NI-4-bromo-3-joclphenyl-N'-isopropylbiguanide, characterized in that N3-isoprop @ Tldicyan- diamid is reacted with 4-bromo-3-iodaniline. N'-4-bromo-3-iodophenyl-N'-isopropyl biguanide is a strong base whose monohydrochloride melts at 239.degree. The new base has powerful anti-malarial properties.
CH259703D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259703A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259703X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259703A true CH259703A (en) 1949-01-31

Family

ID=27178059

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259703D CH259703A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259703A (en)

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