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

HRID 884655Notes

Reaction equation

HRID 884655 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:19]=[CH:20][CH:21]=2)[O:14][CH2:15][C:16]([OH:18])=[O:17])=[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:12]=[C:13]([O:14][CH2:15][C:16]([OH:18])=[O:17])[CH:19]=[CH:20][CH:21]=3)[NH:24][C:25](=[O:26])[N:27]=2)=[CH:4][C:3]=1[CH3:23]

Participants

5

Reactant 2

HCID 1176UreaHCID 57831167(E)-2-(3-(3-(4-hydroxy-3-methylphenyl)-3-oxoprop-1-enyl)phenoxy)acetic acid

Product 1

HCID 178422597({3-[6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]phenyl}oxy)acetic acidYield 54.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

(E)-2-(3-(3-(4-Hydroxy-3-methylphenyl)-3-oxoprop-1-enyl)phenoxy)acetic acid (15.0 g, 48.0 mmol) and urea (14.4 g, 0.24 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 and heated in a 90° C. oil bath for 10 minutes, then cooled down to room temperature by itself. The suspension was filtered, washed with 50 mL of 2-propanol and dried in the air. 9.2 g (54%) of yellow powder was obtained. 1H NMR (400 MHz, DMSO-d6): δ 10.39 (s, 1H), 8.00 (s, 1H), 7.90 (m, 1H), 7.75 (m, 1H), 7.65 (s, 1H), 7.40-7.55 (m, 2H), 7.16 (m, 1H), 6.95 (m, 1H), 4.80 (s, 2H), 2.20 (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-4711f60a010b43beb179243fe0c2ba53
Source dataset
uspto-grants-2012_08
Patent number
US08242129B2

Reaction notes

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