Methanol → HCID 68542093, compound

HRID 1442581Notes

Reaction equation

HRID 1442581 reaction equation
O=C1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]1=[CH:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18].[C:22](=[O:25])([O-])[O-:23].[Na+].[Na+].[CH3:28]O>>[C:5]([NH:4][C:3](=[CH:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:16]([C:17]#[N:18])[CH:15]=1)[C:22]([O:23][CH3:28])=[O:25])(=[O:6])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 10340Sodium CarbonateHCID 68543765HCID 68543765, compound

Product 1

HCID 68542093HCID 68542093, compoundYield 74%

Procedure

A suspension of 3-[(5-oxo-2-phenyl-1,3-oxazol-4(5H)-ylidene)-methyl]benzonitrile (1.98 g, 9.01 mmol) and sodium carbonate (26 mg, 0.25 mmol) in methanol was heated under reflux for 2.5 hours. After the reaction mixture was concentrated under reduced pressure, ethyl acetate and water were added to the residue to separate the organic layer. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and concentrated under reduced pressure. The residue was applied to silica gel column chromatography (gradient elution with hexane-ethyl acetate from 80:20 to 33:67) and recrystallized from acetone-diisopropyl ether to give the title compound (1.63 g, 74%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. concentrationAfter the reaction mixture was concentrated under reduced pressure, ethyl acetate and water
  4. additionwere added to the residue
  5. customto separate the organic layer
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. washThe combined organic layers were washed with water
  8. concentrationconcentrated under reduced pressure
  9. washThe residue was applied to silica gel column chromatography (gradient elution with hexane-ethyl acetate from 80:20 to 33:67)
  10. customrecrystallized from acetone-diisopropyl ether

Sources & evidence

ORD record
ord-bf31f50bc60a449dafc9ad1a26dcc1dd
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

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