Sodium hydride → HCID 59481239, compound

Participants

Reaction Steps

To a solution of N-benzyl-4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxamide (0.30 g, 0.95 mmol) in N,N-dimethylformamide (15 mL) was added sodium hydride (60% in mineral oil, 0.38 g, 0.95 mmol). The reaction mixture was stirred at ambient temperature for 30 minutes. To the resulting solution was added 4-fluorobenzoyl chloride (0.11 mL, 0.95 mmol). The reaction mixture was stirred at ambient temperature for 16 hours and concentrated in vacuo. The residue was dissolved in dichloromethane (50 mL) and washed with water. The organic layer was dried over anhydrous sodium sulphate, filtered, and concentrated in vacuo. The residue was purified by column chromatography eluted with 60-80% ethyl acetate in hexanes to afford the title compound in 23% yield (0.10 g, 23%): mp 130-132° C.; 1H NMR (300 MHz, CDCl3) δ 7.66-7.61 (m, 2H), 7.29-7.23 (m, 5H), 7.10-7.04 (m, 2H), 5.86 (br s, 1H), 4.49 (d, J=5.5 Hz, 2H), 4.21-4.15 (m, 4H), 2.60 (s, 3H), MS (ES+) m/z 439.2 (M+1).

Provenance & Evidence