Thionyl Chloride → 2-Chlorobenzo[d]oxazole-4-carbonitrile

Temperature

80 °C

A mixture of 2-sulfanyl-1,3-benzoxazole-4-carbonitrile (178 mg), thionyl chloride (427 mg) and DMF (0.0468 mL) was stirred at 80° C. for 5 min. The reaction mixture was concentrated under reduced pressure, ethyl acetate and THF were added, and the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate, and the extract was washed with distilled water and brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with diisopropyl ether to give the title compound (178 mg).

1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate and THF
2. additionwere added
3. extractionThe mixture was extracted with ethyl acetate
4. washthe extract was washed with distilled water and brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customthe solvent was evaporated under reduced pressure
7. washThe residue was washed with diisopropyl ether

ORD record

ord-7a4444ad589f4d2d886d10d2d9f915a4

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722662B2