CH259690A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259690A
CH259690A CH259690DA CH259690A CH 259690 A CH259690 A CH 259690A CH 259690D A CH259690D A CH 259690DA CH 259690 A CH259690 A CH 259690A
Authority
CH
Switzerland
Prior art keywords
chloro
preparation
biguanide derivative
acid
salts
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 CH259690A publication Critical patent/CH259690A/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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (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-          @-1iromphenyl-N'-äthylbiguanid,    welches ein  wertvolles     eheinotherapeutisehes    Mittel ist;  oder als     Zwisehenprodukt    für die Herstellung  von chemotherapeutischen Mitteln verwendet  werden kann. Es ist insbesondere ein wert  volles     Antimalariamittel.     



       Erfindungsgemäss    wird die besagte neue  Verbindung,     nämlieli        N'-4-Chlor-3-bromphent-1-          N'-äthy        lbiguanid,    dadurch erhalten, dass man       N'-Rthyldieyandiamid    mit     4-Chlor-3-broni-          anilin    umsetzt.  



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



  Das     N'-4-Chl.or-3-bromphenyl-N'-ätli@#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 sieh     dadureb    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.     Aeeton,    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,        Methansulfonsäure.          lIetliylendisalicylsäure,        Methylen-bis-ss-oxy-          naphthoesäure    und Salzsäure bequem her  stellen.  



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.    <I>Beispiel:</I>  Ein     C_Temisch    von 123 Teilen     NI--Ä.thyl-          dieyandiainid    und     \?4,3    Teilen     4-Chlor-3-brom-          anilin-chlorhydrat    in 100 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 Äthyl  aeetat gewaschen und aus Wasser umkristalli  siert.

   Auf diese Weise erhält man     N'-4-Chlor-          3        .-bromphenyl-N'-ä.thyl.bibuanid    in Form  seines     1GIonohydrochlorids,    welches bei 215 bis  216  C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of Nl-4-chloro- @ -1iromphenyl-N'-ethylbiguanide, which is a valuable eheinotherapeutisehes agent; or as an intermediate product for the manufacture of chemotherapeutic agents. It is a particularly valuable antimalarial drug.



       According to the invention, the said new compound, namely N'-4-chloro-3-bromophene-1-N'-ethy lbiguanide, is obtained by reacting N'-rthyldieyandiamide with 4-chloro-3-bronianiline.



  The reaction is conveniently carried out by heating a salt of the amine with the substituted dieyandiamide in the presence of a solvent, such as. B. NNTasser or ss-ethoxyethanol.



  The N'-4-Chl.or-3-bromphenyl-N'-ätli@#l- biguanid 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 more convenient in dry form by mixing the components in an organic solvent, such as

   B. Aeeton, or in an alcohol in which the salts are sparse Lich soluble, are prepared. In this way you can, for example, the salts with acetic acid, lactic acid, methanesulfonic acid. Ethylene disalicylic acid, methylene-bis-ss-oxynaphthoic acid and hydrochloric acid can be conveniently prepared.



  The following example serves to explain the invention. <I> Example: </I> A C_Temisch of 123 parts of NI - Ä.thyl- dieyandiainid and \? 4.3 parts of 4-chloro-3-bromo-aniline-chlorohydrate in 100 parts of ß-ethoxy ethanol is during Heated to boiling under reflux for 3 hours. The mixture is then allowed to cool and it is filtered off. The solid residue is washed with cold ethyl acetate and recrystallized from water.

   In this way, N'-4-chloro-3-bromophenyl-N'-ä.thyl.bibuanid is obtained in the form of its 1Gionohydrochloride, which melts at 215-216 ° C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N1-4-Chlor- ;-broniphenyl-N1-ät.hylbigLianid, dadurch ge kennzeichnet, dass man N3-Äthy ldieyandiamid mit 4-Chlor-3-bromanilinumsetzt. Das N'-4-Chlor-3-brompheiiyl-N'-äthyl- bigua.nid ist eine starke Base, deren Mono hydroehlorid bei 21.5 bis 216 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigen- schaften. PATENT CLAIM: Process for the preparation of N1-4-chloro-; -broniphenyl-N1-ät.hylbigLianid, characterized in that N3-Äthy ldieyandiamid is reacted with 4-chloro-3-bromaniline. The N'-4-chloro-3-brompheiiyl-N'-äthyl- bigua.nid is a strong base whose monohydrochloride melts at 21.5 to 216 ° C. The new base has powerful antimalarial properties.
CH259690D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259690A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259690X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259690A true CH259690A (en) 1949-01-31

Family

ID=27178046

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259690D CH259690A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259690A (en)

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