Hydrochloric Acid → 1-(5-Chloro-2-methoxyphenyl)-5-phenyl-2,4-imidazolidinedione

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Reaction Steps

N-(5-Chloro-2-methoxyphenyl)urea (1 g, 5 mmol) and phenylglyoxal monohydrate (760 mg, 5 mmol) were taken up in absolute ethanol (100 ml) and acetic acid (1 ml) and 1 ml of conc. HCl added. The reaction mixture was heated at reflux 3.5 h and allowed to stand at 24° C. for 18 h prior to concentration by rotary evaporation. The residue was dissolved in ethyl acetate, washed with sat'd NaHCO3 solution and brine. Recrystallization from methylene chloride/hexanes gave 1 g (63%) mp 200° C.; IR(KBr, υ=cm−1) 3168, 3064, 1772, 1701, 1504, 1444, 1426, 1408, 1260, 1190, 1150; 1H NMR (300 MHz, CDCl3) δ 3.59 (3H, s), 5.60 (1H, s), 6.80 (1H, d, J=8.8 Hz), 7.14-7.37 (7H, m), 8.92 (1H, br.s); MS(DCl)m/z: 317(MH+); Anal. calcd. for C16H13ClN2O3: C, 60.67; H, 4.13; N, 8.84. Found: C,60.47; H, 4.12; N, 8.80.

Provenance & Evidence