CH204735A - Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. - Google Patents
Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.Info
- Publication number
- CH204735A CH204735A CH204735DA CH204735A CH 204735 A CH204735 A CH 204735A CH 204735D A CH204735D A CH 204735DA CH 204735 A CH204735 A CH 204735A
- Authority
- CH
- Switzerland
- Prior art keywords
- quinoline
- imidazole
- reaction
- dihydride
- substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- -1 imidazole dihydride Chemical compound 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XZUAPPXGIFNDRA-UHFFFAOYSA-N ethane-1,2-diamine;hydrate Chemical compound O.NCCN XZUAPPXGIFNDRA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Verfahren zur Darstellung eines in 2-Stellung substituierten Imidazoldihydrids-(4,ö). Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung eines in 2-Stellung substituierten Imidazoldihydrids- (4,5), welches dadurch gekennzeichnet ist, dass man einen Chinolin-8-ogyacetiminoäther mit Äthylendiamin umsetzt.
Der so gewonnene 8-Chinolinäther des 2-Methylol-imidazoldihydrids-(4,5) bildet ein Hydrochlorid vom F. 190 bis<B>190'.</B>
Die neue Verbindung kann als Arznei mittel verwendet werden.
<I>Beispiel:</I> Das durch Umsetzung der Natriumver- bindung von 8-Ogychinolin mit Chloraceto- nitril erhaltene Nitril wird in das Hydro chlorid des Iminoäthers der Formel
EMI0001.0018
übergeführt. Erwärmt man 7,5 Teile des mit etwas Alkohol versetzten Iminoäthers mit 3 Teilen Äthylendiaminhydrat auf dem Was serbad, so entsteht unter Entwicklung von Ammoniak eine Lösung, aus der sich beim Abkühlen ein Niederschlag abscheidet.
Das salzsaure Salz des gebildeten 8-Chinolin- äthers des 2-Methylolimidazoldihydrids-(4,5) der Formel
EMI0001.0026
wurde durch Umkristallisieren aus einem Gemisch von Methanol und Äther analysen rein erhalten.
An Stelle von Chinolin-8-ogyacetimino- äthyläther kann ebensogut ein anderer Äther, wie z. B. der Methyl-, Propyl- oder. Butyl- äther Verwendung finden.
Statt vom salzsauren Salz des Chinolin-8- ogyacetiminoäthers kann man auch von einem andern Salze, wie z. B. vom bromwasserstoff- sauren, vom schwefelsauren oder vom me- thylschwefelsauren Salz ausgehen.
Process for the preparation of an imidazole dihydride (4, ö) substituted in the 2-position. The present patent relates to a process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position, which is characterized in that a quinoline-8-ogyacetiminoether is reacted with ethylenediamine.
The 8-quinoline ether of 2-methylolimidazole dihydride (4,5) obtained in this way forms a hydrochloride from F. 190 to <B> 190 '. </B>
The new compound can be used as a medicine.
<I> Example: </I> The nitrile obtained by reacting the sodium compound of 8-ogyquinoline with chloroacetonitrile is converted into the hydrochloride of the imino ether of the formula
EMI0001.0018
convicted. If 7.5 parts of the imino ether, mixed with a little alcohol, are heated with 3 parts of ethylenediamine hydrate on the water bath, a solution is formed with the evolution of ammonia, from which a precipitate separates out on cooling.
The hydrochloric acid salt of the 8-quinoline ether formed of 2-methylolimidazole dihydride (4,5) of the formula
EMI0001.0026
was obtained pure by recrystallization from a mixture of methanol and ether analyzes.
Instead of quinoline-8-ogyacetimino- äthyläther, another ether, such as z. B. the methyl, propyl or. Butyl ether are used.
Instead of the hydrochloric acid salt of the quinoline-8- ogyacetiminoäthers one can also use another salt, such as z. B. from the hydrobromic acid, the sulfuric acid or the methylsulfuric acid salt.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH204735T | 1935-07-23 | ||
| CH199906T | 1938-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH204735A true CH204735A (en) | 1939-05-15 |
Family
ID=25723388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH204735D CH204735A (en) | 1935-07-23 | 1935-07-23 | Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH204735A (en) |
-
1935
- 1935-07-23 CH CH204735D patent/CH204735A/en unknown
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