Urea → 4-(6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)benzoic acid

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Reaction Steps

(E)-4-(3-(4-hydroxy-3-methylphenyl)-3-oxoprop-1-enyl)benzoic acid (14.7 g, 52.1 mmol) and urea (15.6 g, 0.26 mol) was suspended in 200 mL of 4N HCl solution in dioxane, and the reaction mixture was heated to reflux overnight, then cooled to room temperature. The resulted mixture was concentrated in vacuo to remove dioxane. The residues were suspended in 20 mL of methanol, filtered and washed with 50 mL of water, and dried in the air. 8.3 g (51%) of 4-(6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)benzoic acid were obtained. 1H NMR (400 MHz, DMSO-d6): 10.25 (s, 1H), 8.28 (m, 2H), 7.92-8.05 (m, 4H), 7.58 (s, 1H), 6.95 (m, 1H), 2.18 (s, 3H). MS (EI) for C18H14N2O4: 323 (MH+).

Provenance & Evidence