CH259662A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259662A
CH259662A CH259662DA CH259662A CH 259662 A CH259662 A CH 259662A CH 259662D A CH259662D A CH 259662DA CH 259662 A CH259662 A CH 259662A
Authority
CH
Switzerland
Prior art keywords
methyl
preparation
diiodophenyl
biguanide derivative
isopropyl
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 CH259662A publication Critical patent/CH259662A/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20Derivatives 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
    • C07C279/24Y being a hetero atom
    • C07C279/26X 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     N'-3,4-Dijocl-          phenyl-N'-methyl-N@'-isopropylbiguanid,    wel  ches ein wertvolles     ehemotherapeutisehes    'Mit  tel ist oder als     Zwisehenprodukt    für die Her  stellung von     ehemotherapeutisehen        @4litteln          verwendet    werden kann. Es ist insbesondere  ein wertvolles     Antimalariamittel.     



  Erfindungsgemäss wird die besagte neue       Verbindung-,    nämlich     N'-3,4-Dijodphenyl-hl'-          methyl-N'-isopropylbiguanid,    dadurch     erbal-          ten,        class    man     N'-lllethyl-N'-isopropy        ldicyan-          diamid    mit.     3,4-Dijodanilin    umsetzt.  



  Die Umsetzung erfolgt zweckmässig durch  Erhitzen eines Salzes des Amins mit dem sub  stituierten     Dicyancliamid    in     Gegenwart    eines  Lösungsmittels, z. B. Wasser oder     ss-Ätho-xy-          ät.hanol.     



  Das     N'-3,4-Dijodphenyl-N'-methyl-l@@'-iso-          propylbiguanid    stellt eine starke Base dar,  welche mit organischen und anorganischen  Säuren beständige Salze ergibt, die in man  chen Fällen in Wasser 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     Lösungsmittel,    wie z. B.  Aceton, oder in einem Alkohol, in welchem  die Salze spärlich löslich sind, hergestellt  werden.

   Auf diese Weise kann man beispiels  weise die Salze mit Essigsäure,     Milehsäure,            Methansulfonsäure,        Methy        lendisalicylsäure,          llethylen-bis-ss-oiynaphthoesäure    und Salz  säure     bequem    herstellen.  



  Das folgende Beispiel diene zur Erläute  rung der     Erfindung.       <I>Beispiel,:</I>  Ein Gemisch von 14 Teilen     N'-Methyl-N'-          isopropyldicyandiamid    und 38,2 Teilen     3,4-          Dijodanilin-chlorhydrat    in 125 Teilen     ss-Äth-          oxyäthanol    wird während 3 Stunden unter       Rückfluss    zum Sieden erhitzt. Hierauf lässt  man das Gemisch abkühlen, worauf     abfiltriert     wird. Der feste Rückstand wird mit kaltem  Äthylalkohol gewaschen und aus Wasser um  kristallisiert.

   Auf diese Weise erhält man       N'-3,4-Dijodphenyl-N'-methyl-N'-isopropyl-          biguanid    in Form seines     Monohydrochlorids,     welches bei 235  C schmilzt.



  process for the production of a biguanide derivative. The present invention relates to. a process for the production of N'-3,4-Dijocl- phenyl-N'-methyl-N @ '- isopropylbiguanid, wel ches a valuable erstotherapeutisehes' means is or can be used as an intermediate product for the manufacture of erstotherapeutisehen @ 4littel . It is a particularly valuable antimalarial drug.



  According to the invention, the said new compound, namely N'-3,4-diiodophenyl-hl'-methyl-N'-isopropylbiguanide, is obtained by adding N'-IIIethyl-N'-isopropyl dicyanodiamide. 3,4-Diiodaniline converts.



  The reaction is conveniently carried out by heating a salt of the amine with the sub-substituted dicyancliamide in the presence of a solvent, e.g. B. water or ss-ethoxy-xy-ethanol.



  The N'-3,4-diiodophenyl-N'-methyl-l @@ '- isopropyl 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 in 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. 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, methanesulfonic acid, methylene disalicylic acid, llethylene-bis-ss-olynaphthoic acid and hydrochloric acid can be conveniently prepared.



  The following example serves to explain the invention. <I> Example: </I> A mixture of 14 parts of N'-methyl-N'-isopropyldicyandiamide and 38.2 parts of 3,4-diiodaniline chlorohydrate in 125 parts of β-ethoxyethanol is refluxed for 3 hours heated to boiling. The mixture is then allowed to cool and it is filtered off. The solid residue is washed with cold ethyl alcohol and crystallized from water.

   In this way, N'-3,4-diiodophenyl-N'-methyl-N'-isopropyl biguanide is obtained in the form of its monohydrochloride, which melts at 235.degree.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N'-3,4-Di- j odphenyl - N' - methyl-N' - isopropylbiguanid, dadurch gekennzeichnet, dass man N'-Methyl- N "-isopropy ldiey andiamid mit 3,4-Dijodanilin umsetzt. Claim: A process for the preparation of N'-3,4-diiodophenyl - N '- methyl-N' - isopropylbiguanide, characterized in that N'-methyl-N "-isopropyl andiamide is mixed with 3,4-diiodaniline implements. Das N'-3,4-Dijodphenyl-N'-methyl-N'-iso- propylbiguanid ist eine starke Base, deren Monohy drochlorid bei 235 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigen- sehaften. N'-3,4-Diiodophenyl-N'-methyl-N'-isopropyl biguanide is a strong base, the monohydrochloride of which melts at 235.degree. The new base has strong antimalarial properties.
CH259662D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259662A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259662X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259662A true CH259662A (en) 1949-01-31

Family

ID=27178018

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259662D CH259662A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259662A (en)

Similar Documents

Publication Publication Date Title
CH259662A (en) Process for the preparation of a biguanide derivative.
CH259653A (en) Process for the preparation of a biguanide derivative.
CH259663A (en) Process for the preparation of a biguanide derivative.
CH259703A (en) Process for the preparation of a biguanide derivative.
CH259654A (en) Process for the preparation of a biguanide derivative.
CH259693A (en) Process for the preparation of a biguanide derivative.
CH259677A (en) Process for the preparation of a biguanide derivative.
CH259698A (en) Process for the preparation of a biguanide derivative.
CH259706A (en) Process for the preparation of a biguanide derivative.
CH259707A (en) Process for the preparation of a biguanide derivative.
CH259689A (en) Process for the preparation of a biguanide derivative.
CH259709A (en) Process for the preparation of a biguanide derivative.
CH259681A (en) Process for the preparation of a biguanide derivative.
CH259658A (en) Process for the preparation of a biguanide derivative.
CH259661A (en) Process for the preparation of a biguanide derivative.
CH259713A (en) Process for the preparation of a biguanide derivative.
CH259665A (en) Process for the preparation of a biguanide derivative.
CH259699A (en) Process for the preparation of a biguanide derivative.
CH259683A (en) Process for the preparation of a biguanide derivative.
CH259708A (en) Process for the preparation of a biguanide derivative.
CH259679A (en) Process for the preparation of a biguanide derivative.
CH259657A (en) Process for the preparation of a biguanide derivative.
CH259664A (en) Process for the preparation of a biguanide derivative.
CH259668A (en) Process for the preparation of a biguanide derivative.
CH259682A (en) Process for the preparation of a biguanide derivative.