Water → HCID 11197062, compound

To a solution of N-(3,5-Dimethoxy-phenyl)-2,2,2-trifluoro-acetamide (31.8 g, 130 mmol) in anhydrous dichloroethane (450 mL), cooled in an ice bath, was added a solution of tin (IV) chloride (29.9 mL, 260 mmol dissolved in 30 mL anhydrous dichloroethane) dropwise over 10 minutes. Acetyl chloride (9.1 mL, 130 mmol) was added slowly, maintaining the temperature of the reaction below 5° C. After stirring 3 hours at room temperature, the reaction was cooled in an ice bath. Water (300 mL) was added, maintaining the temperature of the reaction below 25° C., and the reaction was stirred at room temperature for 18 hours. The reaction mixture was extracted with dichloromethane, and the organic layer was separated, washed with water, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by silica gel column chromatography eluting with 20% to 30% hexanes/ethyl acetate to yield N-(4-Acetyl-3,5-dimethoxy-phenyl)-2,2,2-trifluoro-acetamide (4.8 g, 13%) as a white solid.

1. temperaturemaintaining
2. customthe temperature of the reaction below 5° C
3. temperaturethe reaction was cooled in an ice bath
4. temperaturemaintaining
5. customthe temperature of the reaction below 25° C.
6. stirringthe reaction was stirred at room temperature for 18 hours
7. extractionThe reaction mixture was extracted with dichloromethane
8. customthe organic layer was separated
9. washwashed with water
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. customevaporated under reduced pressure
13. customThe residue was purified by silica gel column chromatography
14. washeluting with 20% to 30% hexanes/ethyl acetate

ORD record

ord-6e04ac450a7b49249b2d3bf6ca536a2c

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07531547B2