CH259656A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259656A
CH259656A CH259656DA CH259656A CH 259656 A CH259656 A CH 259656A CH 259656D A CH259656D A CH 259656DA CH 259656 A CH259656 A CH 259656A
Authority
CH
Switzerland
Prior art keywords
preparation
biguanide derivative
acid
propyl
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 CH259656A publication Critical patent/CH259656A/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)

Description

  

  Verfahren zur Herstellung eines     Biguanidderivates.            I:)ie    vorliegende Erfindung betrifft ein  Verfahren zur Herstellung von     N1-3,4,5-Tri-          clilorplleny    1-N     ,-rl-propy        l.bigtranid,    welches ein.  wertvolles chemotherapeutisches Mittel ist  oder als     Zwischenprodukt    für die     Herstelhrug     von     ehemotherapeutiscllen    Mitteln verwendet  werden kann. Es ist insbesondere ein wert  N olles     Antimalarialnittel.     



       Erfindungsgemäss    wird die besagte neue  Verbindung, nämlich     N1-3,4,5-Trichlorpheny        l-          N#"-n-propyll)igtlairicl,        dadurch    erhalten, dass  man     N:'-n-Pr,opylclicy        andiamid    mit     3,4,5-Tri-          chloranilin    umsetzt.  



  Die     Umsetzunf-    erfolgt zweckmässig durch  Erhitzen eines Salzes des Amins mit dem  substituierten     Dicvandiamid    in Gegenwart  eines Lösungsmittels, wie z. B. Wasser oder       ss-Atlloxyi@tllarlol.     



  Das     N1-3,4,5-Triellloi#phenvl-N5-n-propyl-          binuairid    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 sich dadurch     herstellen,        class    die Base  in     wässrigen    Lösungen der Säure gelöst und  Hierauf das     Wasser    verdampft wird, doch  können sie in trockener Form bequemer  durch     Verrnisellen    der     Komponenten    in einem       organisellen    Lösungsmittel, wie z.

   B.     Aeetoll,     oder in einem Alkohol, in welchem die Salze       spärlich.        lösliell    sind, hergestellt werden. Auf  diese     \"eise    kann     rnan    beispielsweise die Salze         reit    Essigsäure, Milchsäure,     Methansulfon-          säure,        Methylendisalicylsäure,        Methy@en-bis-ss-          oxy        naphthoesäure    und Salzsäure bequem her  stellen.  



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.    <I>Beispiel:</I>    Ein Gemisch von 12,6 Teilen     Nrs-n-Propyl-          dicyandiamid    und 2.5,6 Teilen     3,4,5-Triehlor-          anilin-elrlorhy-drat    in 100 Teilen     ss-Äthoxy-          äthanol    wird während 3 Stunden unter     Riick-          fluss    zum Sieden erhitzt. Hierauf lässt man  das     Clemiseh    abkühlen, worauf     abfiltriert     wird. Der feste Rückstand wird mit kaltem       @thylacetat    gewaschen und aus Wasser um  kristallisiert.

   Auf diese Weise erhält man  N1-3,4,5 -     Trichlorphenyl        -1\T        ,-n-propylbiguanid     in Form seines     Monohy        clroehlorids,    welches  bei     28-229"    C schmilzt.



  Process for the preparation of a biguanide derivative. I:) The present invention relates to a process for the preparation of N1-3,4,5-Triclilorplleny 1-N, -rl-propy l.bigtranid, which a. is a valuable chemotherapeutic agent or can be used as an intermediate in the manufacture of former therapeutic agents. It is especially a valuable antimalarial agent.



       According to the invention, said new compound, namely N1-3,4,5-trichlorophenyl- N # "- n-propyl) igtlairicl, obtained by adding N: '- n-Pr, opylclicyandiamide with 3,4,5 -Tri- chloroaniline converts.



  The Umsetzunf- is conveniently carried out by heating a salt of the amine with the substituted dicvandiamide in the presence of a solvent, such as. B. water or ss-Atlloxyi @ tllarlol.



  The N1-3,4,5-Triellloi # phenvl-N5-n-propyl-binuairide 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 dissolving the components in an organic solvent, such as e.g.

   B. Aeetoll, or in an alcohol in which the salts are sparse. are soluble. In this way, for example, the salts acetic acid, lactic acid, methanesulfonic acid, methylenedisalicylic acid, methylene-bis-oxy-naphthoic acid and hydrochloric acid can be conveniently prepared.



  The following example serves to explain the invention. <I> Example: </I> A mixture of 12.6 parts of Nrs-n-propyl-dicyandiamide and 2.5.6 parts of 3,4,5-triehloraniline-elrlorohydrate in 100 parts of ß-ethoxyethanol heated to boiling under reflux for 3 hours. The clemiseh is then allowed to cool, after which it is filtered off. The solid residue is washed with cold ethyl acetate and recrystallized from water.

   In this way, N1-3,4,5-trichlorophenyl -1 \ T, -n-propylbiguanide is obtained in the form of its monohydric chloride, which melts at 28-229 "C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N1-3,4,5 Trielllop pheny 1-N -n-propy lbiguanicl, dadurch gekennzeichnet, dass man N"-n-PropyIdieya,n- cliamid mit 3,1,5-Trichloranililr umsetzt. Das N1-3,4,5-Triehlorplieiiyl.-N,-li-propyl- biguanid ist eine starke Base, deren Mono hvdroehlorid bei 228-229"C schmilzt. Die neue Base besitzt kräftige Ant.imalariaeigen- sehaften. PATENT CLAIM: Process for the production of N1-3,4,5 Trielllop pheny 1-N -n-propy Ibiguanicl, characterized in that N "-n-PropyIdieya, n-cliamide is reacted with 3,1,5-trichloroanilil N1-3,4,5-Triehlorplieiiyl.-N, -li-propyl-biguanid is a strong base whose monohydrochloride melts at 228-229 "C. The new base has strong antimalarial properties.
CH259656D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259656A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259656X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259656A true CH259656A (en) 1949-01-31

Family

ID=27178012

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259656D CH259656A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259656A (en)

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