CH259708A - Process for the preparation of a biguanide derivative. - Google Patents
Process for the preparation of a biguanide derivative.Info
- Publication number
- CH259708A CH259708A CH259708DA CH259708A CH 259708 A CH259708 A CH 259708A CH 259708D A CH259708D A CH 259708DA CH 259708 A CH259708 A CH 259708A
- Authority
- CH
- Switzerland
- Prior art keywords
- chloro
- preparation
- iodophenyl
- biguanide derivative
- acid
- Prior art date
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 Nl-3-Chlor-4- jodphenyl-N '-ii-hropylbiguaiiid, welches ein wertvolles chemotherapeutisches Mittel ist oder als Zwischenprodukt für die Herstellung von chemotherapeutischen Mitteln verwendet wer den kann. Es ist insbesondere ein wertvolle Antimalariamittel.
Erfindungsgemäss wird die besagte neue Verbindung, nämlich Nl-3-Clilor-4-jodphenyl- N'-n-propylbiguanid, dadurch erhalten, dal man N'-n-Propyldicyandiamid mit 3-Chlor-4- jodanilin umsetzt.
Die Umsetzung erfolgt zweckmässig durch Erhitzen eines Salzes des Amins mit dem substituierten Dicyandiamid in Cegenwart eines Lösungsmittels, wie z. B. Wasser oder ss- Ätho.xyäthanol.
Das NI -3-Chlor-4-jodphenyl-N'-n-propyl- 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 i, wässrigen Lösungen der Säure gelöst und hierauf das Wasser verdampft wird, doch können sie in trockener Form bequemer durch Vermischen der Komponenten in einem orga nischen 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, Nlethylendisalicylsäure, llethylen-bis-ss-oxy- iiaplithoesäure und Salzsäure bequem her stellen.
Das folgende Beispiel diene zur Erläute rung der Erfindung. <I>Beispiel:</I> Ein Gemisch von 12,6 Teilen N3-n-Propyl- dieyandiamid und 32 Teilen 3-Chlor-4- jodanilin-chlorhydrat in 75 Teilen ss-Ä thoxy - äthanol wird während 3 Stunden unter Rückfluss zum Sieden erhitzt. Hierauf lässt man das Gemisch abkühlen, worauf abfil- triert wird.
Der feste Rückstand wird -mit kaltem Äthylacetat gewaschen und aus Was ser umkristallisiert. Auf diese Weise erhält man Nl-3-Chlor-4-jodphenyl-N'-n-propylbigua- nid in Form seines Monohydrochlorids, wel ches bei 225 C schmilzt.
Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of Nl-3-chloro-4-iodophenyl-N '-ii-hropylbiguaiiid, 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 Nl-3-chloro-4-iodophenyl-N'-n-propylbiguanide, is obtained by reacting N'-n-propyldicyandiamide with 3-chloro-4-iodaniline.
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- Ätho.xyäthanol.
The NI -3-chloro-4-iodophenyl-N'-n-propyl-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 prepared in that the base i, aqueous solutions of the acid and then the water is evaporated, but they can be more convenient in dry form by mixing the components in an orga African 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, methylenedisalicylic acid, ethylene-bis-β-oxyiaplithoic acid and hydrochloric acid can be conveniently prepared.
The following example serves to explain the invention. <I> Example: </I> A mixture of 12.6 parts of N3-n-propyl-dieyandiamide and 32 parts of 3-chloro-4-iodaniline chlorohydrate in 75 parts of β-ethoxy ethanol is refluxed for 3 hours 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 water. In this way, Nl-3-chloro-4-iodophenyl-N'-n-propylbiguanide is obtained in the form of its monohydrochloride, which melts at 225.degree.
Claims (1)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB259708X | 1945-10-08 | ||
GB170946X | 1946-09-17 | ||
CH254800T | 1946-10-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH259708A true CH259708A (en) | 1949-01-31 |
Family
ID=27178064
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH259708D CH259708A (en) | 1945-10-08 | 1946-10-08 | Process for the preparation of a biguanide derivative. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH259708A (en) |
-
1946
- 1946-10-08 CH CH259708D patent/CH259708A/en unknown
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