Methyl vinyl sulfone → HCID 44517931, compound

Participants

Reaction Steps

A solution of (S)-1-[4-(4-chloro-phenoxy)-phenyl]-5-(3-trifluoromethyl-phenyl)-imidazolidin-2-one (1.5 g, 3.47 mmol) in anhydrous DMF (20 mL) is cooled down to 0° C. in an ice bath when NaH (194 mg, 60% in mineral oil, 4.86 mmol) is added into the solution portion wise. After the addition, the mixture is stirred at 0° C. for 10 min when a solution of vinyl methylsulfone (736 mg, 6.94 mmol) in DMF (5 mL) is added into the mixture. The resulted mixture is allowed to warm up to room temperature and stir for 1 h. The mixture is then poured into 10% NH4Cl aqueous solution (˜300 mL) and extracted with EtOAc (3×100). The combined organic layer is washed with brine and dried (MgSO4). After removing the drying agent, the solution is concentrated and purified by flash column chromatography (silica gel, EtOAc/hexane 0%˜100%) to provide the desired product (S)-3-[4-(4-chloro-phenoxy)-phenyl]-1-(2-methanesulfonyl-ethyl)-4-(3-trifluoromethyl-phenyl)-imidazolidin-2-one as white solid (1.18 g, 63%) with the recovery of the starting material (S)-1-[4-(4-chloro-phenoxy)-phenyl]-5-(3-trifluoromethyl-phenyl)-imidazolidin-2-one (˜300 mg). 1H NMR (CDCl3, 400 MHz) δ 7.45˜7.58 (m, 4H), 7.29 (d, 2H), 7.23 (d, 2H), 6.87 (m, 4H), 5.27 (dd, 1H), 4.07 (t, 1H), 3.80˜4.10 (m, 2H), 3.28˜3.40 (m, 3H), 3.01 (s, 3H); HPLC-MS calculated for C25H22ClF3N2O4S (M+H+) 539.1, found 539.1.

Provenance & Evidence