2-Aminophenol → 2(3H)-Benzoxazolone

Triethylamine (27.0 mL) was added to a mixture of 2-aminophenol (10 g, 91.74 mmol) in dichloromethane (200 μL) at 5° C. This was followed by the addition of a solution of bis(trichloromethyl) carbonate (9.35 g, 31.48 mmol) in dichloromethane (40 mL), while 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 water. 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.

1. temperaturewhile maintaining 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 water
6. filtrationAfter filtration
7. washthe filter cake was washed with hydrochloric acid (10%) and water

ORD record

ord-980166c689824a3f9428d5710c3a0278

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696229B2