Imidazole → N-p-methoxybenzylimidazole

Temperature

0 °C

To a solution of 10.88 g (0.16 mol) of imidazole in 150 ml of dry DMF at 0° C. under argon was added 6.4 g (0.16 mol) of 60% NaH, and the mixture was stirred at 0° C. for 30 min and then at room temperature for 1 h. The mixture was cooled to 0° C., and 25 g (0.16 mol) of p-methoxybenzyl chloride was added, and the mixture was stirred at room temperature for 24 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between methylene chloride and water. The organic layer was dried over sodium sulfate, concentrated in vacuo to yield 35.6 g of a crude product which was purified by chromatography on silica (methylene chloride/methanol 9:1) to afford 25.3 g (84.2%) of 1-(p-methoxybenzyl)-imidazole.

1. waitat room temperature for 1 h
2. temperatureThe mixture was cooled to 0° C.
3. stirringthe mixture was stirred at room temperature for 24 h
4. concentrationThe reaction mixture was concentrated in vacuo
5. customthe residue was partitioned between methylene chloride and water
6. dry with materialThe organic layer was dried over sodium sulfate
7. concentrationconcentrated in vacuo
8. customto yield 35.6 g of a crude product which
9. customwas purified by chromatography on silica (methylene chloride/methanol 9:1)

ORD record

ord-2f4e5a19526a4540a8074ba76ea65efe

Source dataset

uspto-grants-1997_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05604224