Phosphorus pentachloride → 1-(1,3-diisopropyldibenzo[b,d]furan-2-yl)-2-phenyl-4,5-dihydro-1H-imidazole

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Reaction Steps

N-(2-chloroethyl)benzamide (4.09 g, 22.27 mmol) and 90 mL m-xylene were added to a 250 ml, round-bottom flask. Next, phosphorus pentachloride (6.96 g, 33.4 mmol) was added carefully. The reaction mixture was heated to reflux under nitrogen for 2 h. The reaction mixture was cooled down to room temperature and 1,3-diisopropyldibenzo[b,d]furan-2-amine (6.55 g, 24.50 mmol) in 30 mL m-xylene was added. The reaction mixture was refluxed overnight under nitrogen. The reaction mixture was cooled in an ice bath. White solid was collected by filtration. The solid was washed with hexanes, dissolved in ethyl acetate, and washed twice with 10% sodium hydroxide solution. The organic layer was dried over magnesium sulfate, filtered, evaporated to a white solid which was dried under vacuum. 4.78 g (54% yield) of product was obtained.

Provenance & Evidence