2-Aminophenol → 2(3H)-Benzoxazolone

HRID 641906Notes

Reaction equation

HRID 641906 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15].[C:16](=O)(OC(Cl)(Cl)Cl)[O:17]C(Cl)(Cl)Cl>C(Cl)Cl>[O:15]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:16]1=[O:17]

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 8471TriethylamineHCID 94429Triphosgene

Product 1

HCID 60432(3H)-BenzoxazoloneYield 235.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (27.0 mL) was added to a mixture of 2-aminophenol (10 g, 91.74 mmol) in CH2Cl2 (200 mL) at 5° C. A solution of bis(trichloromethyl) carbonate (9.35 g, 31.48 mmol) in dichloromethane (40 mL) was then added, maintaining the temperature below 10° C. The resulting solution was then maintained below 10° C. for 6 hours. The reaction mixture was then quenched by the addition of water (50 mL) and ethanol (20 mL). After 0.5 hours, the mixture was concentrated and then poured into 400 mL of H2O. After filtration, the filter cake was washed with hydrochloric acid (10%) and water to afford 10 g (48%) of benzo[d]oxazol-2(3H)-one as an off-white solid.

Workup

  1. temperaturemaintaining the temperature below 10° C
  2. temperatureThe resulting solution was then maintained below 10° C. for 6 hours
  3. customThe reaction mixture was then quenched by the addition of water (50 mL) and ethanol (20 mL)
  4. concentrationthe mixture was concentrated
  5. additionpoured into 400 mL of H2O
  6. filtrationAfter filtration
  7. washthe filter cake was washed with hydrochloric acid (10%) and water

Sources & evidence

ORD record
ord-a88fc1f952c54aa2af29b3e1e64ba009
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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