CH271040A - Process for the preparation of a biguanide derivative. - Google Patents
Process for the preparation of a biguanide derivative.Info
- Publication number
- CH271040A CH271040A CH271040DA CH271040A CH 271040 A CH271040 A CH 271040A CH 271040D A CH271040D A CH 271040DA CH 271040 A CH271040 A CH 271040A
- Authority
- CH
- Switzerland
- Prior art keywords
- biguanide
- isopropyl
- preparation
- parts
- biguanide derivative
- 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 eines Biguanid- derivates, nämlich des N1-3,4-Dichlor-phenyl- Nb-isopropyl-biguanids, welches gegen Mala ria wirksam ist.
Das erfindungsgemässe Verfahren ist da durch gekennzeichnet, dass Nl-m-Chlor-phe- nyl-NS-isopropyl-biguanid der Wirkung eines Chlorierungsmittels unterworfen wird.
Überraschenderweise verläuft die Chlo- rierung beim erfindungsgemässen Verfahren glatt und führt zur Bildung des p-Chlorsub- stitutionsproduktes, das in guter Ausbeute erhalten wird. Es wäre eigentlich zu erwarten gewesen, dass durch die Behandlung mit Chlorierungsmitteln ein erheblicher Zerfall der hochaktiven Biguanidinstruktur verur sacht würde.
Als Chlorierungsmittel kann zweckmässi- gerweise Chlor verwendet werden.
Das Verfahren kann zweckmässigerweise unter Verwendung eines flüssigen Mediums, vorzugsweise eines solchen, welches als Lö sungsmittel für die Reaktionsteilnehmer wirkt, beispielsweise von Essigsäure, Nitro- benzol oder konzentrierter Schwefelsäure, durchgeführt werden.
Im folgenden Beispiel bedeuten die Teile Gewichtsteile. <I>Beispiel:</I> 17,73 Teile Nl-m-Chlor-phenyl-NI-isopro- pyl-biguanid werden in 110 Teilen Eisessig gelöst. In die abgekühlte und gerührte Lö sung werden 58 Teile Eisessig, welche 5,0 Teile Chlor enthalten, eingetragen. Man lässt das Gemisch sich auf atmosphärische Tempera tur erwärmen und dann während 17 Stunden stehen. Hierauf trägt man das Reaktions gemisch in 50 Teile Wasser ein und extrahiert mit Benzol. Man giesst die wässerige Schicht nach erfolgter Extraktion in einen Überschuss an 40%iger Natriumhydroxydlösung und ex trahiert das abgeschiedene Öl mit Benzol.
Die Benzollösung wird mit 25 Teilen 7 %iger Salzsäure in 3 Portionen geschüttelt. Die wäs serigen Anteile werden vereinigt, geklärt und durch Zugabe von wässerigem Ammoniak gegen Brillantgelb alkalisch gestellt. Der Nie derschlag wird abfiltriert, mit Wasser ge waschen und aus Wasser umkristallisiert. Durch wiederholte Kristallisation aus Wasser erhält man farblose Kristalle von N1-3,4-Di chlor-phenyl-NS-isopropyl-biguanid-hydro- chlorid vom Smp. 244 C.
Process for the preparation of a biguanide derivative. The present invention relates to a process for the production of a biguanide derivative, namely N1-3,4-dichlorophenyl-Nb-isopropyl-biguanide, which is effective against malaria.
The method according to the invention is characterized in that Nl-m-chloro-phenyl-NS-isopropyl-biguanide is subjected to the action of a chlorinating agent.
Surprisingly, the chlorination proceeds smoothly in the process according to the invention and leads to the formation of the p-chlorine substitution product, which is obtained in good yield. It would actually have been expected that treatment with chlorinating agents would cause considerable disintegration of the highly active biguanidine structure.
Chlorine can conveniently be used as the chlorinating agent.
The process can conveniently be carried out using a liquid medium, preferably one which acts as a solvent for the reactants, for example acetic acid, nitrobenzene or concentrated sulfuric acid.
In the following example, the parts mean parts by weight. <I> Example: </I> 17.73 parts of Nl-m-chloro-phenyl-NI-isopropyl-biguanide are dissolved in 110 parts of glacial acetic acid. 58 parts of glacial acetic acid, which contain 5.0 parts of chlorine, are introduced into the cooled and stirred solution. The mixture is allowed to warm to atmospheric temperature and then stand for 17 hours. The reaction mixture is then added to 50 parts of water and extracted with benzene. After the extraction has taken place, the aqueous layer is poured into an excess of 40% strength sodium hydroxide solution and the oil which has separated out is extracted with benzene.
The benzene solution is shaken with 25 parts of 7% hydrochloric acid in 3 portions. The aqueous components are combined, clarified and made alkaline against brilliant yellow by adding aqueous ammonia. The precipitate is filtered off, washed with water and recrystallized from water. Repeated crystallization from water gives colorless crystals of N1-3,4-dichlorophenyl-NS-isopropyl-biguanide hydrochloride with a melting point of 244 C.
Claims (1)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB271040X | 1946-08-02 | ||
| GB191247X | 1947-12-19 | ||
| GB221247X | 1947-12-22 | ||
| CH266995T | 1948-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH271040A true CH271040A (en) | 1950-09-30 |
Family
ID=27429735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH271040D CH271040A (en) | 1946-08-02 | 1948-02-28 | Process for the preparation of a biguanide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH271040A (en) |
-
1948
- 1948-02-28 CH CH271040D patent/CH271040A/en unknown
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