Urea → HCID 10214785, compound

HRID 2253275Notes

Reaction equation

HRID 2253275 reaction equation
CO[C:3](=[O:19])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.[NH2:20][C:21]([NH2:23])=[O:22].[O-]CC.[Na+]>[Pd].C(O)C>[O:12]([C:9]1[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][C:3]([NH:20][C:21]([NH2:23])=[O:22])=[O:19])=[CH:11][CH:10]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 1176UreaHCID 2723922Sodium ethoxideHCID 54278950HCID 54278950, compound2×

Product 1

HCID 10214785HCID 10214785, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-phenoxy-benzaldehyde was reacted with triethyl phosphonoacetate to yield 3-(4-phenoxyphenyl)-acrylic acid ethyl ester, which was then reduced with H2 using palladium-on-carbon catalyst to yield 3-(4-phenoxyphenyl)-propionic acid methyl ester (19). Urea (1.20 g, 19.99 mmol) was dissolved in sodium ethoxide (2 M, 6.7 mL, 13.4 mmol) at 80° C. under argon, and to this a solution of 19 (1.71 g, 6.67 mmol) in anhydrous ethanol (8 mL) was added and heated at this temperature for 1 hr. Ethanol was evaporated under reduced pressure, water (20 mL) was added, acidified to pH 1 by 5% aqueous HCl and extracted with ethyl acetate (50 mL). The organic layer was washed with water (2×25 mL), brine (2×20 mL), dried over anhydrous magnesium sulfate and evaporated. The crude product was purified by silica gel chromatography and eluted with hexane-ethyl acetate (1:1) containing acetic acid (1%) followed by recrystallization from ethanol. Yield: 113 mg, 5.6%.

Workup

  1. temperatureheated at this temperature for 1 hr
  2. customEthanol was evaporated under reduced pressure, water (20 mL)
  3. additionwas added
  4. extractionextracted with ethyl acetate (50 mL)
  5. washThe organic layer was washed with water (2×25 mL), brine (2×20 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe crude product was purified by silica gel chromatography
  9. washeluted with hexane-ethyl acetate (1:1)
  10. additioncontaining acetic acid (1%)
  11. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-557f850663be410c83f7e2203161f29e
Source dataset
uspto-grants-2008_01
Patent number
US07323496B2

Reaction notes

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