Ethyl Acetate → HCID 9884128, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-benzyl-6-bromo-1,3-dihydro-benzoimidazol-2-one (0.75 g, 2.5 mmol), 3-chloro-phenyl boronic acid (0.4 g, 2.6 mmol), tetrakis(triphenylphosphine)-palladium (0) (0.23 g, 0.2 mmol), and potassium carbonate (0.72 g, 5.2 mmol) in toluene (15 mL) and H2O (8 mL) was subject to a blanket of nitrogen for 15 minutes at 50° C. and then heated to 85° C. for 1 hour. The reaction mixture was cooled to room temperature and ethyl acetate (100 mL) was added. The organic layer was washed twice with aqueous ammonium chloride (30 mL) and once with brine (30 mL), dried over magnesium sulfate and concentrated. After removal of the solvent, the residue was purified via chromatography (silica gel, 25% ethyl acetate/hexane) to give 1-benzyl-6-(3-chloro-phenyl)-1,3-dihydro-benzoimidazol-2-one as a white solid (0.134 g, 16%): mp 168-169° C.; 1H-NMR (DMSO-d6) δ11.0 (s, 1H), 7.66 (t, 1H, J=2.05 Hz), 7.58-7.5 (m, 1H), 7.45 (t, 2H, J=8.18 Hz), 7.37-7.22 (m, 7 H), 7.08 (d, (1H, J=8.18 Hz), 5.1 (s, 2H); MS (ES) m/z 333([M−H]−, 100%); Anal. Calc. For C20H15ClN2O: C, 71.75; H, 4.52; N, 8.37. Found: C, 70.27; H, 4.56; N, 8.0.

Provenance & Evidence