CH259668A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259668A
CH259668A CH259668DA CH259668A CH 259668 A CH259668 A CH 259668A CH 259668D A CH259668D A CH 259668DA CH 259668 A CH259668 A CH 259668A
Authority
CH
Switzerland
Prior art keywords
preparation
biguanide derivative
acid
dichlorophenyl
butylbiguanide
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 CH259668A publication Critical patent/CH259668A/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     N1-3,4-Di-          chlorphenyl-N'-n-butylbiguanid,    welches ein  wertvolles     chemotherapeutisches    Mittel ist  oder als Zwischenprodukt für die Herstel  lung von chemotherapeutischen Mitteln ver  wendet     werden    kann.     Es    ist insbesondere ein  wertvolles     Antimalariamittel.     



  Erfindungsgemäss wird die     besagte    neue  Verbindung, nämlich     N1-3,4-Dichlorphenyl-          N'-n-butylbiguanid"    dadurch erhalten, dass  man     N3-n-Butyldicyandiamid    mit     3,4-Di-          chloranilin        umsetzt.     



  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     N1-3,4.-Dichlorphenyl-N'-n-butylbi-          guanid    stellt eine starke Base dar, welche mit  organischen und anorganischen Säuren be  ständige     Salze    ergibt, die in manchen Fällen  in Wasser leicht löslich sind. Die Salze las  sen 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     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,     Methansul-          fonsäure,        Methylendisa.licylsäure,        Methylen-          bis-ss-oxynaphthoesäure    und Salzsäure be  quem     herstellen.     



  Das, folgende Beispiel diene zur Erläute  rung der Erfindung.         Beispiel:     Ein Gemisch von 15,4 Teilen     N3-n-Butyl-          dicya.ndiamid    und 19,85 Teilen     3,4-Dichlor-          anilin-chlorhydrat    in 100 Teilen     3,4-Dichlor-          anilin    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       Äthylacetat    gewaschen und aus Wasser um  kristallisiert.

   Auf diese Weise erhält man       Ni-3,4-Dich@lorphenyl-N'-n-butylbiguanid    in  Form seines     Monohydrochlorids,    welches bei       i97     C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of N1-3,4-dichlorophenyl-N'-n-butylbiguanide, 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 N1-3,4-dichlorophenyl-N'-n-butylbiguanide ", is obtained by reacting N3-n-butyldicyandiamide with 3,4-dichloroaniline.



  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 N1-3,4.-dichlorophenyl-N'-n-butylbiguanide 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 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, methanesulphonic acid, methylenedisalicylic acid, methylene bis-β-oxynaphthoic acid and hydrochloric acid can be easily prepared.



  The following example serves to explain the invention. Example: A mixture of 15.4 parts of N3-n-butyl-dicya.ndiamide and 19.85 parts of 3,4-dichloro-aniline chlorohydrate in 100 parts of 3,4-dichloro-aniline is refluxed for 3 hours to Boiling heated. 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, Ni-3,4-dichlorophenyl-N'-n-butylbiguanide is obtained in the form of its monohydrochloride, which melts at 97.degree.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N1-3,4-Di- ,hlorphenyl-N'-n-butylbi,guanid, dadurch ge kennzeichnet, dass man N3-n-Butyldicyan- liamid mit 3,4-Dichloranilin umsetzt. Das N1-3,4-Dichlorphenyl-N'-n-butylbi- ;uanid ist eine starke Base, deren Mono iydrochlorid bei<B>197'</B> C schmilzt. Die neue Base besitzt kräftige Antimalariaeigenschaf- ben. PATENT CLAIM: Process for the production of N1-3,4-di-, chlorophenyl-N'-n-butylbi, guanide, characterized in that N3-n-butyldicyaniliamide is reacted with 3,4-dichloroaniline. The N1-3,4-dichlorophenyl-N'-n-butylbi-; uanide is a strong base, the monohydrochloride of which melts at <B> 197 '</B> C. The new base has strong antimalarial properties.
CH259668D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259668A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259668X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259668A true CH259668A (en) 1949-01-31

Family

ID=27178024

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259668D CH259668A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259668A (en)

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