Hydrochloric Acid → 5-chloro-2-(4-nitrophenyl)-1H-Imidazole-4-carboxaldehyde

Reaktionsgleichung

[ClH:1].[N+:2]([C:5]1[CH:18]=[CH:17][C:8]([CH:9]=[N:10][C:11](=[C:14](Cl)Cl)[C:12]#[N:13])=[CH:7][CH:6]=1)([O-:4])=[O:3].[O:19]1CCOCC1>>[Cl:1][C:12]1[N:13]=[C:9]([C:8]2[CH:17]=[CH:18][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=2)[NH:10][C:11]=1[CH:14]=[O:19]

Komponenten

Edukt 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 122907202-(4-Nitrobenzylidene)amino-3,3-dichloropropenonitrile

Produkt 1

HCID 1785200115-chloro-2-(4-nitrophenyl)-1H-Imidazole-4-carboxaldehyde

Versuchsvorschrift

HCl gas was bubbled through a solution of 2-(4-nitrobenzylidene)amino-3,3-dichloro-propenonitrile (40.0 g, 0.148 mole) in dioxane (500 ml) at room temperature. The mixture was stirred for 23 hours at 50 ΕC. HCl gas was bubbled through followed by stirring for 24 hours at 50 ΕC. The mixture was stirred for 8 more days at 50 ΕC with addition of HCl-gas every 24 hours, followed by stirring at 50 ΕC for 4 more days. More HCl-gas was added and stirred for 3 more days at 50 ΕC. The solution was cooled to 0 ΕC and filtered. The residue was mixed with ethanol (96%, 200 ml) and the title compound, Compound 6, was isolated by filration. Yield: 23.1 g (62%). NMR confirmed the structure of the title compound.