CH259674A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259674A
CH259674A CH259674DA CH259674A CH 259674 A CH259674 A CH 259674A CH 259674D A CH259674D A CH 259674DA CH 259674 A CH259674 A CH 259674A
Authority
CH
Switzerland
Prior art keywords
preparation
bromophenyl
biguanide derivative
acid
water
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 CH259674A publication Critical patent/CH259674A/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-p-Brom-          phenyl-N'-äthylbiguanid,        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     Nl-p-Bromphenyl-N'-          äthylbiguanid,    dadurch erhalten,     dass    man       N'-Äthy        ldicy        andiamid    mit     p-Bromanilin    um  setzt.  



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



  Das     N'-p-BromphenylyN'-äthylbiguanid     stellt eine     starke    Base dar, welche     mit    orga  nischen und anorganischen Säuren beständige  Salze ergibt. die in manchen Fällen in Was  ser 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     organischen        Lö-          sungsmittel,    wie z. B.

   Aceton, oder in einem  Alkohol, in welchem die Salze spärlich lös  lich sind, hergestellt werden. Auf     diese    Weise    kann man     beispielsweise    die Salze mit Essig  säure,     Milehsäure,        Methansulfonsäure,        Me,-          thylendisalicylsäur    e,     Methylen-bis-fl-oxynaph-          thoesäure    und Salzsäure bequem herstellen.  



  Das folgende     Beispiel    diene zur Erläute  rung der Erfindung.    <I>Beispiel:</I>  Ein     Gemisch    von 4,1 Teilen.     N3-Äthylen-          dicyandiamid    und 8,0 Teilen     p-B'romanilin-          chlorhy        drat    in 20 Teilen     p-Äthoxyäthanol     wird während 3 Stunden     unter        Rückfluss     zum Sieden erhitzt. Hierauf lässt man das  Gemisch     abkühlen,    worauf     abfiltriert    wird.

    Der feste Rückstand wird     mit        kaltem    Was  ser gewaschen und aus Wasser umkristalli  siert. Auf diese Weise erhält man     Ni-p-          Bromphenyl-N'-äthylbiguanid    in Form seines       Monohydrochlorids,    welches bei 233 bis       23411    C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of Nl-p-bromophenyl-N'-ethylbiguanide, 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, the said new compound, namely Nl-p-bromophenyl-N'-ethylbiguanide, is obtained by reacting N'-ethyl iodicyandiamide with p-bromoaniline.



  The implementation takes place. conveniently 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 N'-p-bromophenylyN'-äthylbiguanid 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 produced 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, methylene disalicylic acid, methylene-bis-fl-oxynaphthoic acid and hydrochloric acid can be conveniently prepared.



  The following example serves to explain the invention. <I> Example: </I> A mixture of 4.1 parts. N3-ethylene dicyandiamide and 8.0 parts of p-B'romanilin- chlorohydrate in 20 parts of p-ethoxyethanol is refluxed for 3 hours. The mixture is then allowed to cool and it is filtered off.

    The solid residue is washed with cold water and recrystallized from water. In this way, Ni-p-bromophenyl-N'-ethyl biguanide is obtained in the form of its monohydrochloride, which melts at 233 to 23411.degree.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Nl-p- Bromphenyl-N'-äthylb@iguanid, dadurch ge kennzeichnet, dass man N3-Athyldieyan.- diamid mit p-Bromanilin umsetzt. Das Nl-p@Bromphenyl-,N'-äthylbiguanid ist. eine starke Base, deren Monohydrochlorid bei 233 bis 234 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigenschaften. PATENT CLAIM: Process for the preparation of Nl-p-bromophenyl-N'-ethylb @ iguanid, characterized in that N3-Athyldieyan.- diamide is reacted with p-bromoaniline. The Nl-p @ bromophenyl, N'-ethylbiguanide is. a strong base, the monohydrochloride of which melts at 233 to 234 C. The new base has powerful antimalarial properties.
CH259674D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259674A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259674X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259674A true CH259674A (en) 1949-01-31

Family

ID=27178030

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259674D CH259674A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259674A (en)

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