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

Temperature

80 °C

2-Mercapto-benzoxazol-6-ol (1 eq) was dissolved in thionyl chloride (10 eq). DMF (0.6 eq) was slowly added to this solution at room temperature. The mixture was heated to 80° C. and refluxed for 15 minutes. The reaction mixture was cooled to room temperature and the solvent was removed. The resulting solid was azeotroped three times with xylenes. The solid was dissolved in a 10% solution of THF in ethyl acetate and washed once with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried with anhydrous sodium sulfate, filtered, and the solvent removed. The solid was triturated with acetonitrile to yield pure product with a 68% yield. MH+=170.0.

1. temperaturerefluxed for 15 minutes
2. temperatureThe reaction mixture was cooled to room temperature
3. customthe solvent was removed
4. customThe resulting solid was azeotroped three times with xylenes
5. dissolutionThe solid was dissolved in a 10% solution of THF in ethyl acetate
6. washwashed once with a saturated aqueous solution of sodium bicarbonate
7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
8. filtrationfiltered
9. customthe solvent removed
10. customThe solid was triturated with acetonitrile
11. customto yield pure product with a 68% yield

ORD record

ord-001e380076574698887482670cf33645

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173689B2