4-Chlorophenol → N-[2-(4-Chlorophenoxy)ethyl]-1-methyl-N-(tetrahydro-2H-pyran-4-yl)-1H-imidazole-4-carboxamide

Participants

Reaction Steps

To a mixture of N-(2-hydroxyethyl)-1-methyl-N-(tetrahydro-2H-pyran-4-yl)-1H-imidazole-4-carboxamide (150 mg), p-chlorophenol (114 mg), triphenylphosphine (217 mg) and tetrahydrofuran (3.8 mL), DIAD (172 μL) was added under cooling with ice and the resulting mixture was stirred at room temperature for 3 days. To the reaction mixture, water was added and extraction was conducted with diethyl ether. The diethyl ether layer was dried over anhydrous sodium sulfate. After filtering off the desiccant, the solvents were distilled off under reduced pressure and the resulting residue was purified by column chromatography (silica gel cartridge; chloroform/methanol=99:1 and NH silica gel cartridge; hexane/ethyl acetate=1:3 to 1:9) to give the titled compound (103 mg).

Provenance & Evidence