CH254800A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH254800A
CH254800A CH254800DA CH254800A CH 254800 A CH254800 A CH 254800A CH 254800D A CH254800D A CH 254800DA CH 254800 A CH254800 A CH 254800A
Authority
CH
Switzerland
Prior art keywords
preparation
chlorophenyl
biguanide derivative
water
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 CH254800A publication Critical patent/CH254800A/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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

      Verfahren    zur Herstellung eines     Biguanidderivates.       Die vorliegende Erfindung betrifft     einVer-          fahren    zur     Herstellung    von     Nl-p-Chlorphe-          rivl-N'-is,opropylbiguanid,    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     Ni-p-Chlorphenyl-N6-          i:;opropylbiguanid,    dadurch erhalten,     dass    man       N3-Isopropyldicyandiamid    mit     p-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       P-Äthoxyäthanol.     



  Das     Ni-p-Ch@lorphenyl-N"-isopropylbigua-          nid    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,        Methylendisalicyl:säure,    Methylen-         bis-f-oxynaphthoesäure    und Salzsäure be  quem herstellen.  



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.  



  <I>Beispiel:</I>  Ein Gemisch von 12,6 Teilen     N3-Isopro-          pyldicyandiamid    und 24,6 Teilen     p-Chlor-          anilin-chlorhydrat        in    225     Teilen    Wasser wird  während 3 Stunden unter     Rückfluss    zum Sie  den erhitzt.. Hierauf lässt man das Gemisch       abkühlen,    worauf     abfiltriert    wird.

   Der feste  Rückstand     wird    mit     kaltem    Wasser gewa  schen und aus Wasser     umkristallisiert.    Auf  diese     Weise    erhält man     Nl-p-Chlorphenyl-          N6-isopropylbiguanid    in     Form        seines        Mono-          hydroch,lorids,    welches bei 245   C schmilzt.  Die freie     Base        schmilzt    bei 130 bis 131  C,  ihr     Acetat    bei 188 bis 189  C.



      Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of Nl-p-chlorophe- rivl-N'-is, opropylbiguanide, 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 Ni-p-chlorophenyl-N6- i:; opropylbiguanide, is obtained by reacting N3-isopropyldicyandiamide with p-chloroaniline.



  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 P-ethoxyethanol.



  The Ni-p-chlorophenyl-N "-isopropylbiguanide 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 thereby be made produce that the base is dissolved in aqueous solutions of the acid and then the water is evaporated; but they can be more conveniently in dry form by mixing the components in an organic solvent, such as.

   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, methylenedisalicylic acid, methylene-bis-f-oxynaphthoic acid and hydrochloric acid can be easily prepared.



  The following example serves to explain the invention.



  <I> Example: </I> A mixture of 12.6 parts of N3-isopropyl dicyandiamide and 24.6 parts of p-chloroaniline chlorohydrate in 225 parts of water is refluxed for 3 hours the mixture is allowed to cool and then filtered off.

   The solid residue is washed with cold water and recrystallized from water. In this way, Nl-p-chlorophenyl-N6-isopropylbiguanide is obtained in the form of its monohydrochloride, which melts at 245.degree. The free base melts at 130 to 131 C, its acetate at 188 to 189 C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Nl-p- Chlorphenyl-N"-isopropylbiguanid, dadurch gekennzeichnet, dass man N3-Isopropyldi- eyandiamid mit p-Chloranilin umsetzt. Das -Ni-p-.Chlorphenyl-N6-isopropylbigua- nid ist eine starke Base vom Smp. 130 bis 1310 C, deren Monohydrochlorid bei 244 bis 245 C und deren Acetat bei 188 bis. 189 C schmilzt. Die neue Base besitzt kräftige Antimalarineigenschaften. PATENT CLAIM: A process for the preparation of Nl-p-chlorophenyl-N "-isopropylbiguanide, characterized in that N3-isopropyldi-eyandiamide is reacted with p-chloroaniline. The -Ni-p-chlorophenyl-N6-isopropylbiguanide is a strong one Base with a melting point of 130 to 1310 ° C., the monohydrochloride of which melts at 244 to 245 ° C. and the acetate of which melts at 188 to 189 ° C. The new base has powerful antimalarine properties.
CH254800D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH254800A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB254800X 1945-10-08
GB170946X 1946-09-17

Publications (1)

Publication Number Publication Date
CH254800A true CH254800A (en) 1948-05-31

Family

ID=26252458

Family Applications (1)

Application Number Title Priority Date Filing Date
CH254800D CH254800A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH254800A (en)

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