CH259683A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259683A
CH259683A CH259683DA CH259683A CH 259683 A CH259683 A CH 259683A CH 259683D A CH259683D A CH 259683DA CH 259683 A CH259683 A CH 259683A
Authority
CH
Switzerland
Prior art keywords
preparation
bromophenyl
isopropyl
biguanide derivative
water
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 CH259683A publication Critical patent/CH259683A/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 N     I-m-Brom-          phenyl-NS-isopropylbigUanid,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-m-Bromphenyl-NS-          isopropylbiguanid,    dadurch erhalten, dass man       Isopropy        ldicy        andiamid    mit     m.-Bromanilin    um  setzt.  



  Die Umsetzung erfolgt     zweckmässig    durch  Erhitzen eines Salzes des Amins mit dem sub  stituierten     Dicyandiamid    in Gegenwart eine  Lösungsmittels, wie z. B. Wasser oder     ss-          Äthoxyäthanol.     



  Das     NI        -m-Bromphenyl-NS-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 lassen  sich dadurch herstellen, dass die Base in     wäss-          rigen    Lösungen der Säure gelöst und hierauf  das Wasser verdampft wird, doch können sie       iri.    trockener Form bequemer durch Ver  mischen der Komponenten in einem organi  schen Lösungsmittel, wie z. B. Aceton, oder  in einem Alkohol, in welchem die Salze spär  lich löslich sind, hergestellt werden.

   Auf diese    Weise kann man beispielsweise die Salze mit  Essigsäure, Milchsäure,     Methansulfonsäure,          llethylendisalicylsäure,        Alethylen-bis-ss-oxy-          x:aphthoesäure    und Salzsäure bequem her  stellen.  



  Das folgende Beispiel diene zur Erläu  terung der Erfindung.    <I>Beispiel:</I>  Ein Gemisch von 7,25 Teilen     N3-Isopropyl-          dicy        andiamid    und 10,4 Teilen     m-Bromanilin-          ehlorhydrat    in 16 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 gewaschen  und aus Wasser umkristallisiert.

   Auf diese  Weise erhält man     NI-m-Bromphenyl-NS-iso-          propylbiguanid    in Form seines     Monohydro-          chlorids,    welches bei 225 C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of N I-m-bromophenyl-NS-isopropylbigUanide, 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-m-bromophenyl-NS-isopropyl biguanide, is obtained by reacting isopropyl dicyandiamide with m.-bromoaniline.



  The reaction is conveniently carried out by heating a salt of the amine with the sub-substituted dicyandiamide in the presence of a solvent, such as. B. water or ss- ethoxyethanol.



  The NI -m-bromophenyl-NS-isopropylbigua- nide 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 produced by dissolving the base in aqueous solutions of the acid and then evaporating the water, but they can be iri. dry form more convenient by mixing the components in an organic solvent, such as. B. acetone, or in an alcohol in which the salts are sparse Lich soluble, are produced.

   In this way, for example, the salts with acetic acid, lactic acid, methanesulfonic acid, llethylene disalicylic acid, alethylene-bis-ss-oxy-x: aphthoic acid and hydrochloric acid can be conveniently prepared.



  The following example serves to explain the invention. <I> Example: </I> A mixture of 7.25 parts of N3-isopropyl dicyandiamide and 10.4 parts of m-bromaniline ehlorhydrat in 16 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 with cold water and recrystallized from water.

   In this way, NI-m-bromophenyl-NS-isopropyl biguanide is obtained in the form of its monohydrochloride, which melts at 225.degree.

Claims (1)

PATENTANSPRUCFI Verfahren zur Herstellung von NI-m- Bromphenyl-N6-isopropylbiguanid, dadurch gekennzeichnet, dass man N#'-Isopropyldicyan- diamid mit m-Bromanilin umsetzt. Das NI-m-Bromphenyl-NI-isopropylbigua- nid ist eine starke Base, deren Monohydro- ehlorid bei 225 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigensehaften. PATENT CLAIMS Process for the preparation of NI-m-bromophenyl-N6-isopropyl biguanide, characterized in that N # '- isopropyl dicyanodiamide is reacted with m-bromoaniline. NI-m-bromophenyl-NI-isopropylbiguanide is a strong base, the monohydrochloride of which melts at 225.degree. The new base has strong anti-malarial properties.
CH259683D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259683A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259683X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259683A true CH259683A (en) 1949-01-31

Family

ID=27178039

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259683D CH259683A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259683A (en)

Similar Documents

Publication Publication Date Title
CH259683A (en) Process for the preparation of a biguanide derivative.
CH259713A (en) Process for the preparation of a biguanide derivative.
CH254800A (en) Process for the preparation of a biguanide derivative.
CH259681A (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.
CH259707A (en) Process for the preparation of a biguanide derivative.
CH259703A (en) Process for the preparation of a biguanide derivative.
CH259679A (en) Process for the preparation of a biguanide derivative.
CH259699A (en) Process for the preparation of a biguanide derivative.
CH259666A (en) Process for the preparation of a biguanide derivative.
CH259693A (en) Process for the preparation of a biguanide derivative.
CH259661A (en) Process for the preparation of a biguanide derivative.
CH259698A (en) Process for the preparation of a biguanide derivative.
CH259674A (en) Process for the preparation of a biguanide derivative.
CH259662A (en) Process for the preparation of a biguanide derivative.
CH259677A (en) Process for the preparation of a biguanide derivative.
CH259706A (en) Process for the preparation of a biguanide derivative.
CH259668A (en) Process for the preparation of a biguanide derivative.
CH259708A (en) Process for the preparation of a biguanide derivative.
CH259670A (en) Process for the preparation of a biguanide derivative.
CH259682A (en) Process for the preparation of a biguanide derivative.
CH259653A (en) Process for the preparation of a biguanide derivative.
CH259673A (en) Process for the preparation of a biguanide derivative.
CH259714A (en) Process for the preparation of a biguanide derivative.