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

HRID 884652Notes

Reaction equation

HRID 884652 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

5

Reactant 2

HCID 1176UreaHCID 57831170(E)-3-(3-(4-hydroxy-3-methylphenyl)-3-oxoprop-1-enyl)benzoic acid

Product 1

HCID 1784225943-(6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)benzoic acidYield 48%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

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, dried in the air. 8.1 g (48%) of a yellowish powder was obtained. 1H NMR (400 MHz, DMSO-d6): δ 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): 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 2-propanol
  7. customdried in the air

Sources & evidence

ORD record
ord-ef3d2537cd9046c3aae6bafa4a729753
Source dataset
uspto-grants-2012_08
Patent number
US08242129B2

Reaction notes

Loading…