Methyl iodide → 2,2,2-trifluoro-N-(4-iodophenyl)-N-methylacetamide

HRID 2113067Notes

Reaction equation

HRID 2113067 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=1)=[O:4].[C:15](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[F:14][C:2]([F:1])([F:13])[C:3]([N:5]([C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=1)[CH3:15])=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6869622,2,2-trifluoro-N-(4-iodophenyl)acetamide

Product 1

HCID 210712382,2,2-trifluoro-N-(4-iodophenyl)-N-methylacetamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Part B: The above-obtained amide was dissolved in acetone (80 mL), to which potassium carbonate (15.75 g, 114.1 mmol) and iodomethane (9.6 mL, 114.1 mmol) were added. The reaction was heated to reflux for 2 hours and cooled, and the resulting solid was filtered. The solvent was removed from the filtrate. The residue was dissolved in dichloromethane, washed with water and brine, and dried over sodium sulfate. After filtration and removal of solvent, the solid was further dried in vacuo to give the desired 2,2,2-trifluoro-N-(4-iodo-phenyl)-N-methyl-acetamide as a white solid. MS found: (M+1)+=330.05.

Workup

  1. additionwere added
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 2 hours
  4. temperaturecooled
  5. filtrationthe resulting solid was filtered
  6. customThe solvent was removed from the filtrate
  7. dissolutionThe residue was dissolved in dichloromethane
  8. washwashed with water and brine
  9. dry with materialdried over sodium sulfate
  10. filtrationAfter filtration and removal of solvent
  11. customthe solid was further dried in vacuo

Sources & evidence

ORD record
ord-254cfaed66bd4b019abbf61d3172b1b8
Source dataset
uspto-grants-2009_04
Patent number
US07524863B2

Reaction notes

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