Sodium hydride → HCID 19006056, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen blanket and at room temperature, 5.8 g of 4-(3,3-dimethyl-1-proplyoxy)-phenol in 20 ml of anhydrous dimethylformamide is dripped into 0.79 g of 80% strength sodium hydride in 50 ml of anhydrous dimethylformamide. After hydrogen evolution has subsided, the mixture is stirred for a further hour at 60° C. Subsequently, 6.12 g of 1-chloromethyl-4,5-dichloroimidazole in 20 ml of anhydrous dimethylformamide is dripped in at room temperature. The whole is then stirred for 3 hours at 80° C. and overnight at room temperature. The mixture is then poured into 100 ml of ice water, followed by extraction three times with methyl tert-butyl ether. The organic phases are washed with 5% strength sodium hydroxide solution and three times with water, dried over sodium sulfate and concentrated under reduced pressure. The residue is recrystallized from cyclohexane. There is obtained 7.4 g of 1-[4-(3,3-dimethyl-1-propyloxy)-phenoxymethyl]-4,5-dichloroimidazole having a melting point of 105°-108° C.

Provenance & Evidence