2(3H)-Benzoxazolone → 4-[2-(2-Oxo-1,3-benzoxazol-3(2H)-yl)ethoxy]benzaldehyde

HRID 896481Notes

Reaction equation

HRID 896481 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[O:10][C:8](=[O:9])[NH:7][C:5]=2[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1>CN(C)C=O>[O:9]=[C:8]1[N:7]([CH2:18][CH2:19][O:20][C:21]2[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=2)[C:5]2[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=2[O:10]1

Participants

5

Reactant 3

HCID 60432(3H)-BenzoxazoloneHCID 11430Potassium CarbonateHCID 1431564-(2-Chloroethoxy)benzaldehyde

Product 1

HCID 223511154-[2-(2-Oxo-1,3-benzoxazol-3(2H)-yl)ethoxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve benzoxazolinone (0.024 mol) in dimethylformamide and add potassium carbonate (0.047 mol). Heat at reflux for 20 minutes and then add the compound obtained in Step A (0.021 mol). Stir magnetically at reflux for 80 minutes. Hydrolyse the reaction mixture in 150 ml of water, suction-filter off the resulting precipitate and recrystallise it from a 5/5 cyclohexane/toluene mixture.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 20 minutes
  3. temperatureat reflux for 80 minutes
  4. filtrationHydrolyse the reaction mixture in 150 ml of water, suction-filter off the resulting precipitate
  5. customrecrystallise it from a 5/5 cyclohexane/toluene mixture

Sources & evidence

ORD record
ord-7fe4e1def63840cca8fa5372b59047de
Source dataset
uspto-grants-2005_07
Patent number
US06919362B2

Reaction notes

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