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

HRID 422056Notes

Reaction equation

HRID 422056 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)/[CH:9]=[CH:10]/[C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=2)=[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:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=3)[NH:22][C:23](=[O:24])[N:25]=2)=[CH:4][C:3]=1[CH3:21]

Participants

5

Reactant 2

HCID 1176UreaHCID 57831176(E)-4-(3-(4-hydroxy-3-methylphenyl)-3-oxoprop-1-enyl)benzoic acid

Product 1

HCID 1359001814-(6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)benzoic acidYield 51%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

(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+).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux overnight
  3. concentrationThe resulted mixture was concentrated in vacuo
  4. customto remove dioxane
  5. filtrationfiltered
  6. washwashed with 50 mL of water
  7. customdried in the air

Sources & evidence

ORD record
ord-cf3c8fa2b4df4de0b98a1682bd04c653
Source dataset
uspto-grants-2012_01
Patent number
US08101625B2

Reaction notes

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