CH259698A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259698A
CH259698A CH259698DA CH259698A CH 259698 A CH259698 A CH 259698A CH 259698D A CH259698D A CH 259698DA CH 259698 A CH259698 A CH 259698A
Authority
CH
Switzerland
Prior art keywords
chloro
preparation
bromophenyl
biguanide derivative
biguanide
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 CH259698A publication Critical patent/CH259698A/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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

  Verfahren zur Herstellung eines     Biguanidderivates.       Die vorliegende Erfindung betrifft ein  Verfahren zur Herstellung von     Nl-3-Chlor-4-          bromphenyl-N'-isopropylbiguanid,    welches ein  wertvolles chemotherapeutisches Mittel ist  oder als     Zwischenprodukt    für die Herstellung  von chemotherapeutischen Mitteln verwendet       vrerden    kann. Es ist insbesondere ein wert  volles     Antimalariamittel.     



  Erfindungsgemäss wird die besagte neue       Verbindung,    nämlich     Nl-3-Chlor-4-bromphenyl-          N5-isopropyIbiguanid,    dadurch erhalten, dass  man     N'-Isopropyldicyandiamid    mit     3-Chlor-4-          bromanilin    umsetzt.  



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



  Das     Nl-3-Chlor-4-bromphenyl-N'        -isopropy        l-          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 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.-          nisehen    Lösungsmittel, wie z. B.

   Aceton, oder  in einem Alkohol, in welchem die Salze     spär-          lieh        löslieh    sind, hergestellt werden. Auf diese  Weise kann     nian    beispielsweise die Salze mit.    Essigsäure, Milchsäure,     Methansulfonsäure,          llethylendisalicylsäure,        Methylen-bis-ss-oxy-          naphthoesäure    und Salzsäure bequem her  stellen.  



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.  



  <I>Beispiel:</I>  Ein Gemisch von<B>12,6</B> Teilen     N3-Iso-          propy        ldieyandiamid    und 24,3 Teilen     4-Brom-          3-chloranilin-chlorhi-drat    in 75 Teilen ss  Athoxyä.thanol wird während 3     Stunden        ante.          Rückfluss    zum Sieden erhitzt. Hierauf lässt  man das Gemisch abkühlen, worauf     abfiltriert     wird. Der feste Rückstand     wird    mit kaltem       -Äthy        lacetat    gewaschen und aus Wasser um  kristallisiert.

   Auf diese Weise erhält man     Nl-          3-Chlor-4-bromphenyl-N'-isopropylbiguanid    in  Form seines     Monohydrochlorids,    welches bei  237  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-N'-isopropyl biguanide, 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-bromophenyl-N5-isopropylbiguanide, is obtained by reacting N'-isopropyldicyandiamide with 3-chloro-4-bromoaniline.



  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-ethoxyethanol.



  The Nl-3-chloro-4-bromophenyl-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, but they can be more conveniently prepared in dry form by mixing the components in an organic solvent, such as, for. B.

   Acetone, or in an alcohol in which the salts are sparsely soluble. In this way nian can, for example, use the salts. Acetic acid, lactic acid, methanesulfonic acid, llethylene disalicylic acid, methylene-bis-ss-oxynaphthoic acid and hydrochloric acid conveniently produce.



  The following example serves to explain the invention.



  <I> Example: </I> A mixture of <B> 12.6 </B> parts of N3-isopropyl dyediamide and 24.3 parts of 4-bromo-3-chloroaniline chlorohydrate in 75 parts of ss ethoxyä .thanol is ante 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, Nl-3-chloro-4-bromophenyl-N'-isopropyl biguanide is obtained in the form of its monohydrochloride, which melts at 237.degree.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N1-3-Chlor- 4-bromphenyl-NS-isopropylbiguanid, dadurch gekennzeichnet, dass man N3-Isopropyldicyan- diamid mit 3-Chlor-4-bromanilin umsetzt. Das Nl-3-Chlor-4-bromphenyl-N'-isopropyl- biguanid ist. eine starke Base, deren Mono livdroehlorid bei 237 C sehmilzt. Die neue Base besitzt. kräftige Antimalariaeigenschaften. PATENT CLAIM: Process for the production of N1-3-chloro-4-bromophenyl-NS-isopropylbiguanide, characterized in that N3-isopropyldicyanodiamide is reacted with 3-chloro-4-bromoaniline. The Nl-3-chloro-4-bromophenyl-N'-isopropyl biguanide is. a strong base, the monofloride of which melts at 237 C. The new base owns. powerful antimalarial properties.
CH259698D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259698A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259698X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259698A true CH259698A (en) 1949-01-31

Family

ID=27178054

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259698D CH259698A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259698A (en)

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