CH259693A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259693A
CH259693A CH259693DA CH259693A CH 259693 A CH259693 A CH 259693A CH 259693D A CH259693D A CH 259693DA CH 259693 A CH259693 A CH 259693A
Authority
CH
Switzerland
Prior art keywords
preparation
biguanide derivative
dibromophenyl
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 CH259693A publication Critical patent/CH259693A/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     N1-3,4-Di-          bi-oinphenyl-N'-isopropylbigttanid,    welches ein       wertvolles    chemotherapeutisches Mittel ist.  oder als Zwischenprodukt für die Herstellung  von chemotherapeutischen Mitteln verwendet  werden kann. Es ist insbesondere ein wertvolles       Antimalariamittel.     



  Erfindungsgemäss wird die besagte neue  Verbindung, nämlich     N1-3,4-Dibromphenyl-N"-          isopropylbiguanid,    dadurch erhalten, dass man       N3-Isopropyldicyandiainid    mit     3,4-Dibrom-          anilin    umsetzt.  



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



  Das     N1-3,4-Dibroniphenyl-N'-isopropyl-          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,     da.ss    die Base  in     wässrigen    Lösungen der Säure gelöst und  hierauf das Wasser verdampft wird, doch  können sie in trockener Form bequemer durch       Verinisehen    der Komponenten in einem orga  nischen Lösungsmittel, wie z. B.     Aeeton,    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,        AIethansulfon-          säure,        Metliylendisalici-lsäure,        Methylen-bis-ss-          oxy        naphthoesäure    und Salzsäure bequem her  stellen.  



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.    <I>Beispiel:</I>    Ein     f'einisch    von 12,6 Teilen     N3-Isopro-          liyldicyandiamid    und 28,8 Teilen     3,4-Dibrom-          anilin-chlorhydrat    in 90 Teilen     ss-Äthoxy-          äthanol    wird während 3 Stunden unter Rück  fluss zum Sieden erhitzt.. Hierauf lässt man  das Gemisch abkühlen, worauf     abfiltriert     wird. Der feste Rückstand wird mit kaltem       tlthvlaeetat    gewaschen und aus Wasser um  kristallisiert.

   Auf diese Weise erhält. man     Nl-          3,4-Dibromphenyl-N'-isopropylbiguanid    in       Form    seines     Monohydrochlorids,    welches bei  240" C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of N1-3,4-di-bi-oinphenyl-N'-isopropylbigttanide, which is a valuable chemotherapeutic agent. or can be used as an intermediate in the manufacture of chemotherapeutic agents. It is a particularly valuable antimalarial drug.



  According to the invention, said new compound, namely N1-3,4-dibromophenyl-N "- isopropylbiguanide, is obtained by reacting N3-isopropyldicyandiainide with 3,4-dibromoaniline.



  The reaction is expediently 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- Äthoxyät.hanol.



  The N1-3,4-dibroniphenyl-N'-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 by dissolving the base in aqueous solutions of the acid and then evaporating the water, but they can be more conveniently prepared in dry form by verifying the components in an organic solvent such as B. Aeeton, or in an alcohol in which the salts are sparse Lich soluble, are prepared.

   In this way, for example, the salts with acetic acid, lactic acid, ethanesulfonic acid, methylenedisalicic acid, methylene-bis-oxy-naphthoic acid and hydrochloric acid can be conveniently prepared.



  The following example serves to explain the invention. <I> Example: </I> A fine of 12.6 parts of N3-isopropyldicyandiamide and 28.8 parts of 3,4-dibromoaniline chlorohydrate in 90 parts of ß-ethoxyethanol is added for 3 hours Reflux heated to boiling. The mixture is then allowed to cool, after which it is filtered off. The solid residue is washed with cold tlthvlaeetat and crystallized from water.

   That way it gets. one Nl-3,4-dibromophenyl-N'-isopropylbiguanide in the form of its monohydrochloride, which melts at 240 "C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N'-3,4-Di- bromphenyl-N'-isopropylbiguanid, dadurch gekennzeichnet, da.ss man :\ '-Isopropt-ldicyan- dia.mid mit 3,4-Dibromanilin umsetzt. Das N1-3,4-Dibromphenyl-N'-isopropyl- biguanid ist eine starke Base, deren Mono- hydroehlorid bei 240 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigenschaften. PATENT CLAIM: A process for the preparation of N'-3,4-dibromophenyl-N'-isopropylbiguanide, characterized in that: \ '-Isopropt-ldicyandia.mid is reacted with 3,4-dibromaniline. N1-3,4-dibromophenyl-N'-isopropyl biguanide is a strong base, the monohydrochloride of which melts at 240.degree. The new base has powerful anti-malarial properties.
CH259693D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259693A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259693X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259693A true CH259693A (en) 1949-01-31

Family

ID=27178049

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259693D CH259693A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259693A (en)

Similar Documents

Publication Publication Date Title
CH259693A (en) Process for the preparation of a biguanide derivative.
CH259698A (en) Process for the preparation of a biguanide derivative.
CH259666A (en) Process for the preparation of a biguanide derivative.
CH259661A (en) Process for the preparation of a biguanide derivative.
CH259699A (en) Process for the preparation of a biguanide derivative.
CH259658A (en) Process for the preparation of a biguanide derivative.
CH259668A (en) Process for the preparation of a biguanide derivative.
CH259703A (en) Process for the preparation of a biguanide derivative.
CH259689A (en) Process for the preparation of a biguanide derivative.
CH259662A (en) Process for the preparation of a biguanide derivative.
CH259707A (en) Process for the preparation of a biguanide derivative.
CH259665A (en) Process for the preparation of a biguanide derivative.
CH259681A (en) Process for the preparation of a biguanide derivative.
CH259704A (en) Process for the preparation of a biguanide derivative.
CH259660A (en) Process for the preparation of a biguanide derivative.
CH259677A (en) Process for the preparation of a biguanide derivative.
CH259713A (en) Process for the preparation of a biguanide derivative.
CH259663A (en) Process for the preparation of a biguanide derivative.
CH259670A (en) Process for the preparation of a biguanide derivative.
CH259683A (en) Process for the preparation of a biguanide derivative.
CH259700A (en) Process for the preparation of a biguanide derivative.
CH259656A (en) Process for the preparation of a biguanide derivative.
CH259688A (en) Process for the preparation of a biguanide derivative.
CH259654A (en) Process for the preparation of a biguanide derivative.
CH259695A (en) Process for the preparation of a biguanide derivative.