CH259655A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259655A
CH259655A CH259655DA CH259655A CH 259655 A CH259655 A CH 259655A CH 259655D A CH259655D A CH 259655DA CH 259655 A CH259655 A CH 259655A
Authority
CH
Switzerland
Prior art keywords
preparation
trichlorophenyl
biguanide derivative
biguanide
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 CH259655A publication Critical patent/CH259655A/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)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

  

  Verfahren zur Herstellung eines     Biguanidderivates.       Die vorliegende Erfindung betrifft ein  Verfahren zur Herstellung von     N'-3,4,5-Tri-          cfilorpheriyl-N'-isopropylbiguanid,        welches    ein  wertvolles chemotherapeutisches Mittel ist  oder als Zwischenprodukt für die Herstellung  von chemotherapeutischen     Mitteln    verwendet  werden kann. Es ist insbesondere ein wert  volles     Antimalariamittel.     



  Erfindungsgemäss wird die besagte     nette          Verbindung,    nämlich     N1-3,4,5-Trichlorphenyl-          N        '-isopropylbiguanid,        dadurch    erhalten,     da-ss     man     N'-Isopropyldicyandiamid    mit     3,4,5=Tri-          ehloranilin    umsetzt.  



  Die     Unisetzung    erfolgt zweckmässig durch  Erhitzen eines Salzes des     Ainins    mit     dein     substituierten     Dicyandiamid    in Gegenwart  eines Lösungsmittels, wie z. B. Wasser oder       ss-Ätlioxyäthanol.     



  Das     N1-3,4,5-Trichlorphenyl-N'-isopropyl-          biguanid    stellt eine     starke    Base dar, welche  mit organischen und anorganischen Säuren  beständige Salze ergibt, die in manchen  Fällen in     Wasser    leicht löslich sind. Die Salze       lassen    sieh dadurch herstellen, dass die Base  in     wässrigen    Lösungen der Säure     -elöst.        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, Methan-         sulfonsäure,        llethylenclisalicZ-lsäure,        1Iethy-          len-bis-f'-oxynaphthoesäure    und Salzsäure  bequem herstellen.     _     Das folgende Beispiel diene zur Erläute  rung der Erfindung.  



       Beispiel:     Ein Gemisch von 12,6 Teilen     N'-Isopropy        1-          clicyandiamid    und 25,6 Teilen     3,4,5-Trichlor-          anilin-chlorhydrat    in 100 Teilen     wässrigein          @-Äthoxy        äthanol    wird während 3 Stunden  unter     R.ückfluss    zum Sieden erhitzt. Hierauf  lässt man das     CTemisch    abkühlen, -worauf ab  filtriert wird.

   Der feste Rückstand wird mit  kaltem     wässrigem        fl-Ät.hoxyäthanol    gewaschen  und aus     Äthvlalkoliol    umkristallisiert. Auf  diese Weise erhält man     N1-3,4,5-Trichlor-          phenyl-N')-isopropylbiguanid    in Form seines       1lonohydroclilorids,    welches bei 254-255  C  schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of N'-3,4,5-tricfilorpheriyl-N'-isopropylbiguanide, 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 nice compound, namely N1-3,4,5-trichlorophenyl-N'-isopropylbiguanide, is obtained by reacting N'-isopropyldicyandiamide with 3,4,5 = trichloroaniline.



  The unisposition takes place conveniently by heating a salt of the amine with your substituted dicyandiamide in the presence of a solvent, such as. B. water or ß-Ätlioxyäthanol.



  N1-3,4,5-trichlorophenyl-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 produced by dissolving the base in aqueous solutions of the acid. and then the water is evaporated, but they can be more conveniently obtained in dry form by mixing the components in an organic solvent such as e.g. 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, methanesulphonic acid, ethylene-clisalic-lic acid, ethylene-bis-f'-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 N'-isopropyl-1-cicyandiamide and 25.6 parts of 3,4,5-trichloroaniline chlorohydrate in 100 parts of aqueous @ -ethoxyethanol is refluxed for 3 hours under R. heated. The C mixture is then allowed to cool, after which it is filtered off.

   The solid residue is washed with cold aqueous fl-Ät.hoxyäthanol and recrystallized from Äthvlalkoliol. In this way, N1-3,4,5-trichlorophenyl-N ') - isopropyl biguanide is obtained in the form of its 1lonohydrochloride, which melts at 254-255.degree.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von NI-3,4,5- Trichlorphenyl-N'-isopropylbigIta.nid, dadurch gekennzeichnet, dass man N'-Isopropylclieyan- diamid mit 3,4,5-Triehloranilin umsetzt. Das N 1-3,4,5-Trichlor phenyl-N'-isol;ropy 1- biguanid ist eine starke Base. deren Mono- liZ#drochlorid bei 25-I-255 C schmilzt. PATENT CLAIM: Process for the production of NI-3,4,5-trichlorophenyl-N'-isopropylbigIta.nid, characterized in that N'-isopropylclieyaniamide is reacted with 3,4,5-triehloraniline. The N 1-3,4,5-trichlorophenyl-N'-isol; ropy 1-biguanide is a strong base. the monolizyl chloride of which melts at 25-125C. Die neue Base besitzt kräftige Antimalar iaeigen- schaften. The new base has strong antimalarial properties.
CH259655D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259655A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259655X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259655A true CH259655A (en) 1949-01-31

Family

ID=27178011

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259655D CH259655A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259655A (en)

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