CH259668A - Process for the preparation of a biguanide derivative. - Google Patents
Process for the preparation of a biguanide derivative.Info
- Publication number
- CH259668A CH259668A CH259668DA CH259668A CH 259668 A CH259668 A CH 259668A CH 259668D A CH259668D A CH 259668DA CH 259668 A CH259668 A CH 259668A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- biguanide derivative
- acid
- dichlorophenyl
- butylbiguanide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 4
- 150000004283 biguanides Chemical class 0.000 title description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 2
- 230000000078 anti-malarial effect Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- -1 N1-3 Chemical class 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- SWHSXWLSBBYLGM-UHFFFAOYSA-N 2-[(2-carboxyphenoxy)methoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCOC1=CC=CC=C1C(O)=O SWHSXWLSBBYLGM-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical class NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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 N1-3,4-Di- chlorphenyl-N'-n-butylbiguanid, welches ein wertvolles chemotherapeutisches Mittel ist oder als Zwischenprodukt für die Herstel lung von chemotherapeutischen Mitteln ver wendet werden kann. Es ist insbesondere ein wertvolles Antimalariamittel.
Erfindungsgemäss wird die besagte neue Verbindung, nämlich N1-3,4-Dichlorphenyl- N'-n-butylbiguanid" dadurch erhalten, dass man N3-n-Butyldicyandiamid mit 3,4-Di- chloranilin 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 N1-3,4.-Dichlorphenyl-N'-n-butylbi- guanid 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 las sen sich 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, Methansul- fonsäure, Methylendisa.licylsäure, Methylen- bis-ss-oxynaphthoesäure und Salzsäure be quem herstellen.
Das, folgende Beispiel diene zur Erläute rung der Erfindung. Beispiel: Ein Gemisch von 15,4 Teilen N3-n-Butyl- dicya.ndiamid und 19,85 Teilen 3,4-Dichlor- anilin-chlorhydrat in 100 Teilen 3,4-Dichlor- anilin 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-3,4-Dich@lorphenyl-N'-n-butylbiguanid in Form seines Monohydrochlorids, welches bei i97 C schmilzt.
Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of N1-3,4-dichlorophenyl-N'-n-butylbiguanide, 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 N1-3,4-dichlorophenyl-N'-n-butylbiguanide ", is obtained by reacting N3-n-butyldicyandiamide 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 N1-3,4.-dichlorophenyl-N'-n-butylbiguanide 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 by dissolving the base in aqueous solutions of the acid and then evaporating the water, 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, methanesulphonic acid, methylenedisalicylic acid, methylene bis-β-oxynaphthoic acid and hydrochloric acid can be easily prepared.
The following example serves to explain the invention. Example: A mixture of 15.4 parts of N3-n-butyl-dicya.ndiamide and 19.85 parts of 3,4-dichloro-aniline chlorohydrate in 100 parts of 3,4-dichloro-aniline is refluxed for 3 hours to Boiling heated. 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-3,4-dichlorophenyl-N'-n-butylbiguanide is obtained in the form of its monohydrochloride, which melts at 97.degree.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB259668X | 1945-10-08 | ||
| GB170946X | 1946-09-17 | ||
| CH254800T | 1946-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH259668A true CH259668A (en) | 1949-01-31 |
Family
ID=27178024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH259668D CH259668A (en) | 1945-10-08 | 1946-10-08 | Process for the preparation of a biguanide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH259668A (en) |
-
1946
- 1946-10-08 CH CH259668D patent/CH259668A/en unknown
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