CH259669A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259669A
CH259669A CH259669DA CH259669A CH 259669 A CH259669 A CH 259669A CH 259669D A CH259669D A CH 259669DA CH 259669 A CH259669 A CH 259669A
Authority
CH
Switzerland
Prior art keywords
preparation
biguanide derivative
dichlorophenyl
acid
biguanide
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 CH259669A publication Critical patent/CH259669A/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.            Die    vorliegende Erfindung     betrifft    ein  Verfahren zur Herstellung von     N1-3,4-Di-          chlorphenyl-N',N'-.di-ätliylbiguanid,    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        Antima.lariamittel.     



  Erfindungsgemäss wird die besagte neue  Verbindung, nämlich     N1-3,4-Diclilorphenyl-          N',N'-di-äthylbiguanid,    dadurch     erhalten,     dass am     N",N''-Di-äthyldicyandiainid    mit 3,4  Diehloranilin 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-Äthoxyäthailol.     



  Das     N1-3,4-Dichlorphenyl-N',N'-di-äthyl-          biguanid        stellt.    eine starke     Base    dar, welche  mit organischen und anorganischen Säuren       beständige    Salze ergibt, die in manchen Fäl  len in Wasser leicht löslich sind. Die Salze       lassen    sich dadurch herstellen, dass die Base  in     -,\-ässrigen        Lösung    n 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,        Methylendisalicylsäure,        Methylen-          bis-ss-oxynaphthoesäure    und Salzsäure be  quem     herstellen.     



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.    <I>Beispiel:</I>  Ein     Gemisch    von 15,4 Teilen     N3,N3-Di-          äthyldicyandiamid    und 19,85 Teilen     3,4-Di-          chloranilin-chlorhydrat    in 100 Teilen ss  Ä.thoxyäthanol wird während 3 Stunden un  ter     Rückfluss    zum Sieden erhitzt. Hierauf  lässt man das Gemisch abkühlen, worauf     ab-          filtriert    wird. Der feste     Rückstand        wird    mit  kaltem     Äthylacetat    gewaschen und aus Was  ser umkristallisiert.

   Auf diese Weise erhält  man     N1-3,4-Dichlorphen:yl-N',N'-di-äthylbi-          guanid    in Form seines     Monohydrochlorids,     welches bei 231  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' -. Di-ätliylbiguanid, which is a valuable chemotherapeutic agent or can be used as an intermediate for the preparation of chemotherapeutic agents . In particular, it is a valuable antimalarial drug.



  According to the invention, said new compound, namely N1-3,4-diclilorphenyl-N ', N'-di-ethyl biguanide, is obtained by reacting on N ", N" -di-ethyl dicyandiainide with 3,4 diehloraniline.



  The reaction is expediently 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-Äthoxyäthailol.



  The N1-3,4-dichlorophenyl-N ', N'-di-ethyl 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 prepared by dissolving the base in -, \ - aqueous solution 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. <I> Example: </I> A mixture of 15.4 parts of N3, N3-diethyldicyandiamide and 19.85 parts of 3,4-dichloroaniline chlorohydrate in 100 parts of .thoxyethanol is under for 3 hours Reflux heated to boiling. The mixture is then allowed to cool, whereupon it is filtered off. The solid residue is washed with cold ethyl acetate and recrystallized from What water.

   In this way, N1-3,4-dichlorophen: yl-N ', N'-di-ethylbiguanide is obtained in the form of its monohydrochloride, which melts at 231.degree.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N1-3,4-Di- chlorphenyl-N',N'-di-äthylbigu.anid, dadurch gekennzeichnet, dass man N',N3-Di-äthyldi- cyandia.mid mit 3,4-Dichloranilin umsetzt. Das N1-3,4-Dichlorphenyl-N',N'-di-äthyl- biguanid ist eine starke Base, deren Mono- hydrochlorid bei 231 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigenschaf- ten. PATENT CLAIM: Process for the production of N1-3,4-dichlorophenyl-N ', N'-di-äthylbigu.anid, characterized in that N', N3-di-äthyldi- cyandia.mid with 3,4 Dichloroaniline converts. N1-3,4-dichlorophenyl-N ', N'-di-ethyl biguanide is a strong base, the monohydrochloride of which melts at 231.degree. The new base has strong antimalarial properties.
CH259669D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259669A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259669X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259669A true CH259669A (en) 1949-01-31

Family

ID=27178025

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259669D CH259669A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259669A (en)

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