Water → HCID 11197062, compound

HRID 1915984Notes

Reaction equation

HRID 1915984 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[Sn](Cl)(Cl)(Cl)Cl.[C:23](Cl)(=[O:25])[CH3:24].O>C(Cl)Cl>[C:23]([C:8]1[C:7]([O:9][CH3:10])=[CH:6][C:5]([NH:11][C:12](=[O:17])[C:13]([F:14])([F:16])[F:15])=[CH:4][C:3]=1[O:2][CH3:1])(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 24287Tin tetrachlorideHCID 885871HCID 885871, compound

Product 1

HCID 11197062HCID 11197062, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-7f0334c4a9d14a81aa3b6fc341014133
Source dataset
uspto-grants-2013_12
Patent number
US08617517B2

Reaction notes

Loading…