Carbon Disulfide → 5-Chloro-2-mercaptobenzoxazole

2-Amino-4-chlorophenol (5.0 g, 35 mmol) and potassium hydroxide (2.34 g, 41.8 mmol) were dissolved in carbon disulfide (50 mL) and EtOH (75 mL), and the reaction mixture was heated to reflux. After 7 h, the reaction mixture was concentrated under reduced pressure. The material was taken up in EtOAc (100 mL) and 1M HCl (50 mL). The aqueous layer was separated, and the organic layer was washed with water (50 mL) and brine (50 mL). The organics were dried over Na2SO4, filtered, and concentrated under reduced pressure, yielding 5.71 g (89%) of the desired product as a brown solid. LC-MS: RT=7.60 min., [M+H]+=186.1.

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. customThe aqueous layer was separated
3. washthe organic layer was washed with water (50 mL) and brine (50 mL)
4. dry with materialThe organics were dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure

ORD record

ord-40b5ccca7b9440798e0219a301e1c6cf

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943622B2