CH259650A - Process for the preparation of a biguanide derivative. - Google Patents
Process for the preparation of a biguanide derivative.Info
- Publication number
- CH259650A CH259650A CH259650DA CH259650A CH 259650 A CH259650 A CH 259650A CH 259650D A CH259650D A CH 259650DA CH 259650 A CH259650 A CH 259650A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- biguanide derivative
- base
- water
- 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Herstellung eines Biguanidderivates. Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von NI-p-Chlor- hhenyl-N'-n-propylbiguanid, welches eile 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-p-Chlorphenyl-N'-n- propylbiguanid, dadurch erhalten, dass man N'-n-Propyldicyandianlid mit p-Chloranilin umsetzt.
Die Umsetzung erfolgt. zweckmässig durch Erhitzen eines Salzes des Amins mit den -i substituierten Dicyandiamid in Gegenwart eines Lösungsmittels, wie z. B. Wasser oder ss-Äthoxyäthanol.
Das NI-p-Clllorphenyl-N'-n-propylbigizanid stellt eine starke Base dar, welche mit orga nischen und anorganischen Säuren beständige Salze ergibt, die in manchen Fällen in Wasser leicht löslich sind. Die Salze lassen sieh da durch 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 Lö sungsmittel, wie z. B. Aceton, oder in eitlem Alkohol, in welchem die Salze spärlich lös lich sind, hergestellt werden.
Auf diese Weise kann man beispielsweise die Salze mit Essig säure, Milchsäure, Methansulfonsäure, Methy- lendisalicylsäitre, Methylen-bis-ss-oxynaphthoe- säure und Salzsäure bequem herstellen.
Das folgende Beispiel diene zur Erläute rung der Erfindung.
<I>Beispiel:</I> Ein Gemisch von 12,6 Teilen N '-n-Pr opy 1 dicyandiamid und 24,6 Teilen p-Chloranilin- chlorhy drat in 200 Teilen Wasser wird wäh rend 3 Stunden unter Rückfloss zum Sieden erhitzt. Hierauf lässt man das Gemisch ab kühlen, worauf abfiltriert wird. Der feste Rückstand wird mit kaltem Wasser gewa schen und aus Wasser umkristallisiert.
Auf diese Weise erhält man NI-p-Chlorphenyl-N'- n-propylbigtianid in Form seines Monohy dro- ehlorids, welches in die Base übergeführt wird, die, aus wässrigem Äthy lall#:ohol um kristallisiert, bei 58,5-60" C schmilzt.
Process for the preparation of a biguanide derivative. The present invention relates to a process for the production of NI-p-chloro-hhenyl-N'-n-propylbiguanide, which is a valuable chemotherapeutic agent or used as an intermediate for the preparation of chemotherapeutic agents. can be. It is a particularly valuable antimalarial drug.
According to the invention, said new compound, namely NI-p-chlorophenyl-N'-n-propyl biguanide, is obtained by reacting N'-n-propyldicyandianlide with p-chloroaniline.
The implementation takes place. Conveniently by heating a salt of the amine with the -i substituted dicyandiamide in the presence of a solvent, such as. B. water or ss-ethoxyethanol.
The NI-p-Clllorphenyl-N'-n-propylbigizanid 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 the fact that the base is dissolved in 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 organic solvent, such as. B. acetone, or in vain alcohol, in which the salts are sparsely soluble Lich, are prepared.
In this way, for example, the salts with acetic acid, lactic acid, methanesulfonic acid, methylene disalicylic acid, methylene-bis-ß-oxynaphthoic 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 N'-n-Pr opy 1 dicyandiamide and 24.6 parts of p-chloroaniline chlorohydrate in 200 parts of water is heated to boiling under reflux 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-p-chlorophenyl-N'-n-propylbigtianide is obtained in the form of its monohydrochloride, which is converted into the base, which crystallizes from aqueous ethyl alcohol at 58.5-60 "C is melting.
Claims (1)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB259650X | 1945-10-08 | ||
GB170946X | 1946-09-17 | ||
CH254800T | 1946-10-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH259650A true CH259650A (en) | 1949-01-31 |
Family
ID=27178006
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH259650D CH259650A (en) | 1945-10-08 | 1946-10-08 | Process for the preparation of a biguanide derivative. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH259650A (en) |
-
1946
- 1946-10-08 CH CH259650D patent/CH259650A/en unknown
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