Ethanol → 5-chloro-6-sulfanyl-3H-benzooxazol-2-one

Zinc dust (14.4 g, 0.22 mol) was added to a solution of mercuric chloride (2.86 g, 10.6 mmol) in water (42 mL) and concentrated hydrochloric acid (1.7 mL). The mixture was stirred for 15 min and the supernatant poured off. The residue was washed with water (2×15 mL), ethanol (2×15 mL) and diethyl ether (2×15 mL). 5-chloro-6-chlorosulfonyl-3H-benzooxazol-2-one (12.3 g, 46 mmol) and ethanol (70 mL) were added to the residue and the mixture placed in an ice-bath. Concentrated hydrochloric acid (36 mL) was added via addition funnel over 15 min and the resulting mixture stirred at reflux for 18 hours. The cooled reaction mixture was poured into ice-cold water (300 mL) and stirred for 20 min. The precipitate was collected to give 9.5 g of a white powder.

1. additionthe supernatant poured off
2. washThe residue was washed with water (2×15 mL), ethanol (2×15 mL) and diethyl ether (2×15 mL)
3. customthe mixture placed in an ice-bath
4. stirringthe resulting mixture stirred
5. temperatureat reflux for 18 hours
6. customThe cooled reaction mixture
7. stirringstirred for 20 min
8. customThe precipitate was collected

ORD record

ord-bacaeb19753345c7bcda78bacff7004c

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06284774B1