Dimethylformamide → 2-Chloro-1,3-benzoxazol-6-OL

Temperature

80 °C

To a suspension of 2-sulfanyl-1,3-benzoxazol-6-ol (1.00 g) in thionyl chloride (4.36 mL) was added DMF (0.278 mL), and the mixture was stirred with heating at 80° C. for 5 min. After allowing to cool to room temperature, the mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate/THF (1:1), and the solution was washed with saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was triturated with acetonitrile. The obtained powder was washed with diisopropyl ether to give the title compound (483 mg).

1. temperatureto cool to room temperature
2. concentrationthe mixture was concentrated under reduced pressure
3. dissolutionThe residue was dissolved in ethyl acetate/THF (1:1)
4. washthe solution was washed with saturated aqueous sodium hydrogen carbonate solution
5. dry with materialdried over anhydrous sodium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customthe obtained residue was triturated with acetonitrile
8. washThe obtained powder was washed with diisopropyl ether

ORD record

ord-10f03558e02d4503a6aaca23a4963dfe

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703758B2