CH259714A - Process for the preparation of a biguanide derivative. - Google Patents
Process for the preparation of a biguanide derivative.Info
- Publication number
- CH259714A CH259714A CH259714DA CH259714A CH 259714 A CH259714 A CH 259714A CH 259714D A CH259714D A CH 259714DA CH 259714 A CH259714 A CH 259714A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- bromo
- iodophenyl
- isopropylbiguanide
- biguanide derivative
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 150000004283 biguanides Chemical class 0.000 title description 2
- 239000000155 melt Substances 0.000 claims description 2
- 230000000078 anti-malarial effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 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
- 239000000203 mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- -1 3-bromo-4-iodaniline-chlorohydrate Chemical compound 0.000 description 1
- HBCBLDVYTZWYLL-UHFFFAOYSA-N 3-bromo-4-iodoaniline Chemical compound NC1=CC=C(I)C(Br)=C1 HBCBLDVYTZWYLL-UHFFFAOYSA-N 0.000 description 1
- 229940123208 Biguanide Drugs 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
- 239000003430 antimalarial agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000007787 solid 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Verfahren zur Herstellung eines Biguanidderivates. Die vorliegende Erfindung betrifft, ein Verfahren zur Herstellung von N'-3-Brom-4- jodphenyl - N'- in etliyl - N' - isopi'opylbiguanid, welches ein wertvolles chemotherapeutisches Mittel ist oder als Zwisehenprodukt für die Herstellung von chemotherapeutischen Mitteln verwendet werden kann. Es ist insbesondere ein wertvolles Antimalariamittel.
Erfinclungsgemäss wird die besagte neue Verbindung, nämlich N1-3-Brom-4-jodphenyl- N'-niethyl-N '-isopropylbiguanid, dadurch er lialten, dass man N'-lletliyl-N'-isopropyl- dieyanclianiid mit 3-Brom-4-jodanilin -umsetzt.
Die Umsetzung erfolgt nveckmässig durch Erhitzen eines Salzes des minn mit dem sub stituierten Dieyandiamid in Gegenwart eines Lösungsmittels, wie z. B. Wasser oder ss- Äthoxyäthanol.
Das Nl-3-Brom-4-jodphenyl-N'-methyl-N'- isopropylbiguanid stellt eine starke Base dar, welche mit organischen und anorganischen Säuren beständige Salze ergibt, die in man chen Fällen in Wasser leicht. löslich sind. Die Salze lassen 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 orga nischen Lösungsmittel, wie z. B. Aceton, oder in einem Alkohol, in welchem die Salze spär lich löslich sind, hergestellt werden.
Auf diese Weise kann man beispielsweise die Salze mit hssigsättre, Milchsäure, 3lethansulfonsäure, Methj-lendisalic3-lsäure, Methylen-bis-f-oxy- naphthoesäure und Salzsäure bequem her stellen.
Das folgende Beispiel diene zur Erläute rung der Erfindung. <I>Beispiel:</I> Ein Gemisch von 13,0 Teilen N3-Methyl- N'-isopropyldicy andiamid und 23,4 Teilen 3- Brom-4-jodanilin-ehlorhydrat in 70 Teilen Wasser 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 Wasser gewaschen und aus Wasser umkri stallisiert.
Auf diese Weise erhält man N1-3 Brom- 4 - jodphenyl -N' - methy 1-N'- isopropyl- biguanid in Form seines Monohydrochlorids, ,v elches bei 232 bis 233 C schmilzt.
Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of N'-3-bromo-4-iodophenyl-N'- in etliyl-N'-isopi'opylbiguanide, which is a valuable chemotherapeutic agent or used as a by-product for the preparation of chemotherapeutic agents can be. It is a particularly valuable antimalarial drug.
According to the invention, the said new compound, namely N1-3-bromo-4-iodophenyl-N'-niethyl-N'-isopropylbiguanide, is produced by adding N'-lletliyl-N'-isopropyl-dieyanclianiide with 3-bromo 4-iodaniline -reacts.
The reaction takes place by heating a salt of the minn with the sub-substituted Dieyandiamid in the presence of a solvent, such as. B. water or ss- ethoxyethanol.
The Nl-3-bromo-4-iodophenyl-N'-methyl-N'-isopropylbiguanide is a strong base which gives stable salts with organic and inorganic acids, which in some cases easily in water. are soluble. 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 convenient in dry form by mixing the components in an orga African solvent, such as. B. acetone, or in an alcohol in which the salts are sparse Lich soluble, are produced.
In this way, for example, the salts with acetic acid, lactic acid, methanesulphonic acid, methj-lendisalic-lic acid, methylene-bis-f-oxynaphthoic acid and hydrochloric acid can be conveniently prepared.
The following example serves to explain the invention. <I> Example: </I> A mixture of 13.0 parts of N3-methyl-N'-isopropyldicyandiamide and 23.4 parts of 3-bromo-4-iodaniline-chlorohydrate in 70 parts of water is refluxed for 3 hours heated to boiling. The mixture is then allowed to cool and it is filtered off. The solid residue is washed with cold water and crystallized umkri from water.
In this way, N1-3 bromine-4-iodophenyl -N'-methy 1-N'-isopropyl biguanide is obtained in the form of its monohydrochloride, which melts at 232 to 233 ° C.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB259714X | 1945-10-08 | ||
| GB170946X | 1946-09-17 | ||
| CH254800T | 1946-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH259714A true CH259714A (en) | 1949-01-31 |
Family
ID=27178070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH259714D CH259714A (en) | 1945-10-08 | 1946-10-08 | Process for the preparation of a biguanide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH259714A (en) |
-
1946
- 1946-10-08 CH CH259714D patent/CH259714A/en unknown
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