CH259664A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259664A
CH259664A CH259664DA CH259664A CH 259664 A CH259664 A CH 259664A CH 259664D A CH259664D A CH 259664DA CH 259664 A CH259664 A CH 259664A
Authority
CH
Switzerland
Prior art keywords
preparation
biguanide derivative
acid
salts
isopropylbiguanide
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 CH259664A publication Critical patent/CH259664A/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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

  Verfahren zur Herstellung eines     Biguanidderivates.       Die vorliegende Erfindung betrifft ein  Verfahren. zur Herstellung von     N1-3,4-Di-          ehlorphenyl-N"-isopropylbiguanid,    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 nette  Verbindung, nämlich     NI-3,4-Dichlorphenyl.-          N        "-isoprop,lbiguanid,    dadurch erhalten, dass  man     N3-Isopropyldieyandiainid    mit     3,4-Di-          ehloranilin    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-Äthoxyäthanol.     



  Das     NI-3,4-Diclilorphenyl-NS-isopropyl-          biguanid    stellt eine starke Base dar, welche  mit organischen und anorganischen Säuren  beständige Salze ergibt, die in manchen  Fällen in Wasser leicht löslich sind. Die Salze  lassen sieh 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 beispielsweise die Salze    mit Essigsäure, Milchsäure,     Methansulfon-          säure,        Methylendisalicylsäizre,        Methylen-bis-ss-          oxynaphthoesäure    und Salzsäure bequem her  stellen.  



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.  



       Beispiel:     Ein Gemisch von 12,6 Teilen     N3-Isopropyl-          dicyandiamid    und 22 Teilen     3,4-Dichlor-          änilin-ehlorhydrat    in 100 Teilen     r)-Äthoxy-          äthanolwird    während 3 Stunden unter     Rüek-          fluss        zum    Sieden erhitzt. Hierauf lässt man  das Gemisch abkühlen, worauf     abfiltriert     wird. Der feste Rückstand wird mit kaltem       Athy        lacetat    gewaschen und aus     Äthylalkohol     umkristallisiert.

   Auf diese Weise erhält man       N1-3,4-Diehlorphenyl-N'-isopropylbiguanid    in  Form seines     Monohydrochlorids,    welches bei       214-245     C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a method. for the preparation of N1-3,4-dichlorophenyl-N "-isopropylbiguanide, 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 agent.



  According to the invention, the said nice compound, namely NI-3,4-dichlorophenyl-N "-isoprop, Ibiguanid, is obtained by reacting N3-isopropyldiyandiainide with 3,4-dichloroaniline.



  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-ethoxyethanol.



  The NI-3,4-diclilorphenyl-NS-isopropyl-biguanid 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. is, 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, methylenedisalicylic acid, methylene-bis-s-oxynaphthoic acid and hydrochloric acid can be conveniently prepared.



  The following example serves to explain the invention.



       Example: A mixture of 12.6 parts of N3-isopropyl dicyandiamide and 22 parts of 3,4-dichloroaniline-chlorohydrate in 100 parts of r) -ethoxyethanol is heated to boiling for 3 hours under reflux. The mixture is then allowed to cool and it is filtered off. The solid residue is washed with cold Athy lacetat and recrystallized from ethyl alcohol.

   In this way, N1-3,4-diehlophenyl-N'-isopropylbiguanide is obtained in the form of its monohydrochloride, which melts at 214-245 ° C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N1-3,4-Di- chlorpheny 1- N j - isopropylbiguanid, dadurch gekennzeichnet, da.ss man N3-Isopropyldicyan- diamid mit 3,4-Dichloranilin umsetzt. Das N1-3,4-Dichlorphenyl-N'-isopropyl- biguanid ist eine starke Base, deren Mono- hydrochlorid bei 244-245 C schmilzt. PATENT CLAIM: Process for the production of N1-3,4-dichloropheny 1- Nj -isopropylbiguanide, characterized in that N3-isopropyldicyanodiamide is reacted with 3,4-dichloroaniline. N1-3,4-dichlorophenyl-N'-isopropyl biguanide is a strong base whose monohydrochloride melts at 244-245 ° C. Die neue Base besitzt kräftige Antimalariaeigen- schaften. The new base has powerful antimalarial properties.
CH259664D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259664A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259664X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259664A true CH259664A (en) 1949-01-31

Family

ID=27178020

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259664D CH259664A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259664A (en)

Similar Documents

Publication Publication Date Title
CH259664A (en) Process for the preparation of a biguanide derivative.
CH259653A (en) Process for the preparation of a biguanide derivative.
CH259658A (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.
CH259654A (en) Process for the preparation of a biguanide derivative.
CH259703A (en) Process for the preparation of a biguanide derivative.
CH259682A (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.
CH259713A (en) Process for the preparation of a biguanide derivative.
CH259662A (en) Process for the preparation of a biguanide derivative.
CH259702A (en) Process for the preparation of a biguanide derivative.
CH259693A (en) Process for the preparation of a biguanide derivative.
CH259706A (en) Process for the preparation of a biguanide derivative.
CH259669A (en) Process for the preparation of a biguanide derivative.
CH259689A (en) Process for the preparation of a biguanide derivative.
CH259656A (en) Process for the preparation of a biguanide derivative.
CH259667A (en) Process for the preparation of a biguanide derivative.
CH259707A (en) Process for the preparation of a biguanide derivative.
CH259655A (en) Process for the preparation of a biguanide derivative.
CH259683A (en) Process for the preparation of a biguanide derivative.
CH259666A (en) Process for the preparation of a biguanide derivative.
CH259714A (en) Process for the preparation of a biguanide derivative.
CH259661A (en) Process for the preparation of a biguanide derivative.