Urea → 3-(6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)benzoic acid
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=[O:15])=[CH:4][C:3]=1[CH3:21].[NH2:22][C:23]([NH2:25])=[O:24]>Cl.O1CCOCC1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:11]3[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=3)[C:14]([OH:16])=[O:15])[NH:22][C:23](=[O:24])[N:25]=2)=[CH:4][C:3]=1[CH3:21]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
(E)-3-(3-(4-hydroxy-3-methylphenyl)-3-oxoprop-1-enyl)benzoic acid (15.0 g, 53.0 mmol) and urea (16.0 g, 0.27 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 150 mL of 2-propanol, filtered and washed with 50 mL of 2-propanol and then dried in the air. 8.1 g (48%) of the desired 3-(6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)benzoic acid was obtained. 1H NMR (400 MHz, DMSO-d6): 10.40 (s, 1H), 8.60 (s, 1H), 8.35 (m, 1H), 8.18 (m, 1H), 8.00 (s, 1H), 7.90 (m, 1H), 7.65 (m, 1H), 7.55 (m, 1H), 6.95 (m, 1H), 2.18 (s, 3H). MS (EI) for C18H14N2O4: 323 (MH+).
Workup
- temperaturethe reaction mixture was heated
- temperatureto reflux overnight
- concentrationThe resulted mixture was concentrated in vacuo
- customto remove dioxane
- filtrationfiltered
- washwashed with 50 mL of 2-propanol
- customdried in the air
Sources & evidence
- ORD record
- ord-b93a8e4cc65745188bd50182a93a7e02
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101625B2
Reaction notes
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