CH259693A - Process for the preparation of a biguanide derivative. - Google Patents
Process for the preparation of a biguanide derivative.Info
- Publication number
- CH259693A CH259693A CH259693DA CH259693A CH 259693 A CH259693 A CH 259693A CH 259693D A CH259693D A CH 259693DA CH 259693 A CH259693 A CH 259693A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- biguanide derivative
- dibromophenyl
- acid
- biguanide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims 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
- QFTJOYLPELHHCO-UHFFFAOYSA-N 3,4-dibromoaniline Chemical compound NC1=CC=C(Br)C(Br)=C1 QFTJOYLPELHHCO-UHFFFAOYSA-N 0.000 claims description 2
- 229940123208 Biguanide Drugs 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 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
- -1 N1-3 Chemical class 0.000 description 2
- 239000002253 acid Substances 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
- 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
- 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
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010992 reflux Methods 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- bi-oinphenyl-N'-isopropylbigttanid, welches ein wertvolles chemotherapeutisches Mittel ist. oder als Zwischenprodukt für die Herstellung von chemotherapeutischen Mitteln verwendet werden kann. Es ist insbesondere ein wertvolles Antimalariamittel.
Erfindungsgemäss wird die besagte neue Verbindung, nämlich N1-3,4-Dibromphenyl-N"- isopropylbiguanid, dadurch erhalten, dass man N3-Isopropyldicyandiainid mit 3,4-Dibrom- anilin umsetzt.
Die Umsetzung erfolgt zweckmässig durch Erhitzen eines Salzes des Amins mit. dem sub stituierten Dicyandiamid in Gegenwart eines Lösungsmittels, wie z. B. Wasser oder ss- Äthoxyät.hanol.
Das N1-3,4-Dibroniphenyl-N'-isopropyl- 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, da.ss die Base in wässrigen Lösungen der Säure gelöst und hierauf das Wasser verdampft wird, doch können sie in trockener Form bequemer durch Verinisehen der Komponenten in einem orga nischen Lösungsmittel, wie z. B. Aeeton, 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, AIethansulfon- säure, Metliylendisalici-lsäure, Methylen-bis-ss- oxy naphthoesäure und Salzsäure bequem her stellen.
Das folgende Beispiel diene zur Erläute rung der Erfindung. <I>Beispiel:</I> Ein f'einisch von 12,6 Teilen N3-Isopro- liyldicyandiamid und 28,8 Teilen 3,4-Dibrom- anilin-chlorhydrat in 90 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 tlthvlaeetat gewaschen und aus Wasser um kristallisiert.
Auf diese Weise erhält. man Nl- 3,4-Dibromphenyl-N'-isopropylbiguanid in Form seines Monohydrochlorids, welches bei 240" C schmilzt.
Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of N1-3,4-di-bi-oinphenyl-N'-isopropylbigttanide, which is a valuable chemotherapeutic agent. or can be used as an intermediate in the manufacture of chemotherapeutic agents. It is a particularly valuable antimalarial drug.
According to the invention, said new compound, namely N1-3,4-dibromophenyl-N "- isopropylbiguanide, is obtained by reacting N3-isopropyldicyandiainide with 3,4-dibromoaniline.
The reaction is expediently carried out by heating a salt of the amine with. the sub-substituted dicyandiamide in the presence of a solvent, such as. B. water or ss- Äthoxyät.hanol.
The N1-3,4-dibroniphenyl-N'-isopropyl biguanide 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 prepared in dry form by verifying the components in an organic solvent such as B. Aeeton, or in an alcohol in which the salts are sparse Lich soluble, are prepared.
In this way, for example, the salts with acetic acid, lactic acid, ethanesulfonic acid, methylenedisalicic acid, methylene-bis-oxy-naphthoic acid and hydrochloric acid can be conveniently prepared.
The following example serves to explain the invention. <I> Example: </I> A fine of 12.6 parts of N3-isopropyldicyandiamide and 28.8 parts of 3,4-dibromoaniline chlorohydrate in 90 parts of ß-ethoxyethanol is added for 3 hours Reflux heated to boiling. The mixture is then allowed to cool, after which it is filtered off. The solid residue is washed with cold tlthvlaeetat and crystallized from water.
That way it gets. one Nl-3,4-dibromophenyl-N'-isopropylbiguanide in the form of its monohydrochloride, which melts at 240 "C.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB259693X | 1945-10-08 | ||
| GB170946X | 1946-09-17 | ||
| CH254800T | 1946-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH259693A true CH259693A (en) | 1949-01-31 |
Family
ID=27178049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH259693D CH259693A (en) | 1945-10-08 | 1946-10-08 | Process for the preparation of a biguanide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH259693A (en) |
-
1946
- 1946-10-08 CH CH259693D patent/CH259693A/en unknown
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