4-Nitrophenol → HCID 14622571, compound

Participants

Reaction Steps

To a solution of N-(2- dimethylaminoethyl)-N-methyl-4- chloro-3-nitrobenzenesulfonamide (2.2 g, 6.84 mmol) and 4- nitrophenol (0.97 g, 7.0 mmol) in dimethylformamide (30 mL) was added 60% sodium hydride-mineral oil suspension (0.28 g, 7.0 mmol). The resulting solution was stirred at 60° for 20 hours under N2. After concentrating under reduced pressure at 50° , the residue was partitioned between ethyl acetate and water. The ethyl acetate extract was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was flash chromatographed over silica gel and 2.8 g of the nitrophenyl ether eluted with 3% methanol-97% chloroform.

Provenance & Evidence