Urea → ({4-[6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]phenyl}oxy)acetic acid

HRID 884658Notes

Reaction equation

HRID 884658 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)/[CH:9]=[CH:10]/[C:11]2[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:13][CH:12]=2)=[CH:4][C:3]=1[CH3:23].[NH2:24][C:25]([NH2:27])=[O:26]>Cl.O1CCOCC1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:11]3[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:13][CH:12]=3)[NH:24][C:25](=[O:26])[N:27]=2)=[CH:4][C:3]=1[CH3:23]

Participants

5

Reactant 2

HCID 1176UreaHCID 59349176(E)-2-(4-[3-(4-Hydroxy-3-methylphenyl)-3-oxoprop-1-enyl]phenoxy)acetic acid

Product 1

HCID 136052111({4-[6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]phenyl}oxy)acetic acidYield 35.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

(E)-2-(4-[3-(4-Hydroxy-3-methylphenyl)-3-oxoprop-1-enyl]phenoxy)acetic acid (10.0 g, 32.0 mmol) and urea (5.9 g, 0.10 mol) was suspended in 150 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 100 mL of 2-propanol and heated in a 90° C. oil bath for 10 minutes, then let it cooled down to room temperature by itself. The suspension was filtered, washed with 50 mL of 2-propanol and dried in the air. 4.0 g (35%) of yellow powder was obtained. 1H NMR (400 MHz, DMSO-d6): δ 10.76 (s, 1H), 8.15 (s, 1H), 8.04 (s, 1H), 7.94 (d, 1H), 7.46 (s, 1H), 7.13 (d, 2H), 7.03 (d, 1H), 7.03 (d, 1H), 4.86 (s, 2H), 2.21 (s, 3H). MS (EI): 353 (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. temperatureheated in a 90° C. oil bath for 10 minutes
  6. temperaturecooled down to room temperature by itself
  7. filtrationThe suspension was filtered
  8. washwashed with 50 mL of 2-propanol
  9. customdried in the air

Sources & evidence

ORD record
ord-a163c3dbea534e5d8dc1e2140ff91cae
Source dataset
uspto-grants-2012_08
Patent number
US08242129B2

Reaction notes

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