CH259709A - Process for the preparation of a biguanide derivative. - Google Patents
Process for the preparation of a biguanide derivative.Info
- Publication number
- CH259709A CH259709A CH259709DA CH259709A CH 259709 A CH259709 A CH 259709A CH 259709D A CH259709D A CH 259709DA CH 259709 A CH259709 A CH 259709A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- chloro
- biguanide derivative
- acid
- iodophenyl
- 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-N1-äthylbiguanid, 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 nette Verbindung, nämlich Nl-3-Chlor-4-jodphenyl- NI-äthylbiguanid, dadurch erhalten, dass man N'-Äthyldicyandiamid mit 3-Chlor-4-jodanilin. umsetzt.
Die Umsetzung erfolgt zweckmässig durch Erhitzen eines Salzes des Amins mit dem sub stituierten Dicyandiamid in Gegenwart eines Lösungsmittels, wie z. B. Nasser oder Ätlioxyäthanol.
Das Nl-3-Clilor-4-jodpllenyl-N'-äthylbigua- 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 in trockener Form bequemer durch Vermi schen 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, Methansulfonsäure, Methylendisalicylsäure, Methylen-bis-ss-oxy- liaphthoesäure und Salzsäure bequem her stellen.
Das folgende Beispiel diene zur Erläute rung der Erfindung.
<I>Beispiel:</I> Ein Gemisch von 11,2 Teilen N3-Äthyl- dicyandiamid und 29 Teilen 3-Chlor-4-jod- anilin-chlorhydrat in 85 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 Äthylacetat gewaschen und aus Wasser um kristallisiert.
Auf diese Weise erhält man Ni- 3-Chlor-4-jodphellyl-N'-äthylbiguanid in Form seines Monohydrochlorids, welches bei 226 bis 227 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-N1-ethylbiguanide, 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 nice compound, namely Nl-3-chloro-4-iodophenyl-NI-ethylbiguanide, is obtained by reacting N'-ethyldicyandiamide with 3-chloro-4-iodaniline. implements.
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. Nasser or Ätlioxyäthanol.
The Nl-3-Clilor-4-iodoplenyl-N'-ethylbiguanide is a strong base which, with organic and inorganic acids, gives permanent 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, methylenedisalicylic acid, methylene-bis-β-oxy-liaphthoic acid and hydrochloric acid can be conveniently prepared.
The following example serves to explain the invention.
<I> Example: </I> A mixture of 11.2 parts of N3-ethyl dicyandiamide and 29 parts of 3-chloro-4-iodo-aniline chlorohydrate in 85 parts of ss'-ethoxyethanol is reused for 3 hours river heated to the boil. The mixture is then allowed to cool and it is filtered off. The solid residue is washed with cold ethyl acetate and recrystallized from water.
In this way, Ni-3-chloro-4-iodophellyl-N'-ethyl biguanide is obtained in the form of its monohydrochloride, which melts at 226 to 227.degree.
Claims (1)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB259709X | 1945-10-08 | ||
GB170946X | 1946-09-17 | ||
CH254800T | 1946-10-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH259709A true CH259709A (en) | 1949-01-31 |
Family
ID=27178065
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH259709D CH259709A (en) | 1945-10-08 | 1946-10-08 | Process for the preparation of a biguanide derivative. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH259709A (en) |
-
1946
- 1946-10-08 CH CH259709D patent/CH259709A/en unknown
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