CH259678A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259678A
CH259678A CH259678DA CH259678A CH 259678 A CH259678 A CH 259678A CH 259678D A CH259678D A CH 259678DA CH 259678 A CH259678 A CH 259678A
Authority
CH
Switzerland
Prior art keywords
preparation
iodophenyl
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 CH259678A publication Critical patent/CH259678A/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

  

  <B>Verfahren</B>     zur        Herstellung   <B>eines</B>     Bignanidderivates.       Die vorliegende Erfindung     betrifft.    ein  Verfahren zur Herstellung von     Nl-p-Jod-          phenyl-NS-n-propylbiguanid,    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    neue  Verbindung, nämlich     Ni-p-Jodphenyl-NS-n-          propylbiguanid,    da-durch erhalten, dass man       Ng-n-Propyldicyandiamid    mit     p-Jodanilin     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-Äthogyäthanol.     



  Das     N'-p-Jodphenyl-N'-n-propylbiguanid     stellt eine starke     Base    dar, welche mit orga  nischen und anorganischen Säuren beständige  Salze ergibt, die in manchen Fällen in Was  ser leicht löslich sind. Die Salze lassen 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 Lö  sungsmittel, wie z. B. Aceton, oder in einem  Alkohol, in welchem die Salze spärlich lös  lich sind, hergestellt werden.

   Auf diese  Weise kann man beispielsweise die Salze mit    Essigsäure, Milchsäure,     Methan.        ulfonsäure,          Methylendisalicylsäure,        Methylen-bis-ss-ogy-          na.phthoesäure        und    Salzsäure bequem her  stellen.  



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.  



       Beispiel:     Ein Gemisch von 12,6     Teilen,        W-n-Pro-          pyldicyandiamid    und 26 Teilen     p-Jodanilin-          ehlorhydrat    in 38 Teilen Wasser wird wäh  rend 3     Stunden    unter     Rückfluss    zum Sieden  erhitzt. Hierauf lässt man das Gemisch ab  kühlen, worauf     abfiltriert    wird.

   Der feste  Rückstand wird mit     kaltem    Wasser ge  waschen und aus     Wasser        umkristallisiert.     Auf     diese    Weise erhält man     1\"-p-Jodphenyl-          N'-n-propylbiguanid    in Form seines Mono  hydrochlorids, welches bei 222 bis     224 1C     schmilzt.



  <B> Process </B> for producing <B> a </B> bignanide derivative. The present invention relates to. a process for the preparation of Nl-p-iodophenyl-NS-n-propylbiguanide, 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, the said new compound, namely Ni-p-iodophenyl-NS-n-propylbiguanide, is obtained by reacting Ng-n-propyldicyandiamide with p-iodoaniline.



  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-ethogyethanol.



  The N'-p-iodophenyl-N'-n-propylbiguanid 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 in that the base is dissolved in aqueous solutions of the acid and then the water is evaporated, but they can be more convenient in dry form by mixing the components in an organic solvent, such as. B. acetone, or in an alcohol in which the salts are sparselös Lich are prepared.

   In this way you can, for example, the salts with acetic acid, lactic acid, methane. Sulphonic acid, methylenedisalicylic acid, methylene-bis-ss-ogy- na, phthoic acid and hydrochloric acid are conveniently made.



  The following example serves to explain the invention.



       Example: A mixture of 12.6 parts of W-n-propyldicyandiamide and 26 parts of p-iodoaniline chlorohydrate in 38 parts of water is refluxed for 3 hours. The mixture is then left to cool, whereupon it is filtered off.

   The solid residue is washed ge with cold water and recrystallized from water. In this way 1 \ "- p-iodophenyl-N'-n-propylbiguanide is obtained in the form of its monohydrochloride, which melts at 222 to 224 1C.

Claims (1)

PATENTANSPRUCIi Verfahren zur Herstellung von N''-p-Jod- phenyl-NS-n-propylbigua_nid@, dadurch gekenn zeichnet, dass man N3-n-Propyldicyandiamid mit p-Jodanilin umsetzt. Das Nl-p-Jodphenyl-NS-n-propylbiguanid ist eine starke Base, deren Monohydrochlorid bei 222 bis, 224 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigensohaften. PATENT REQUIREMENTS Process for the production of N ″ - p-iodophenyl-NS-n-propylbigua_nid @, characterized in that N3-n-propyldicyandiamide is reacted with p-iodoaniline. Nl-p-iodophenyl-NS-n-propylbiguanide is a strong base, the monohydrochloride of which melts at 222 to .224 ° C. The new base has strong antimalarial properties.
CH259678D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259678A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259678X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259678A true CH259678A (en) 1949-01-31

Family

ID=27178034

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259678D CH259678A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259678A (en)

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