Iodoethane → HCID 20067125, compound

HRID 358891Notes

Reaction equation

HRID 358891 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](I)[CH3:8].[F:10][C:11]1[C:12]([O:25][CH3:26])=[C:13]([CH:21]=[CH:22][C:23]=1[F:24])[NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17]>CN(C)C=O>[F:10][C:11]1[C:12]([O:25][CH3:26])=[C:13]([CH:21]=[CH:22][C:23]=1[F:24])[N:14]([CH2:7][CH3:8])[C:15](=[O:20])[C:16]([F:19])([F:18])[F:17]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 20067155HCID 20067155, compound

Product 1

HCID 20067125HCID 20067125, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

5.66 g (0.041 mole) of potassium carbonate and 6.39 g (0.041 mole) of ethyl iodide were added to a solution of 7.0 g (0.027 mole) of 3,4-difluoro-2-methoxy-N-(trifluoroacetyl)aniline (XI) [prepared as described in Preparation 15 (C1)] dissolved in 130 ml of dimethylformamide. The mixture was then stirred at 70° C. for 5 hours, after which the solvent was distilled off under reduced pressure. The residue was extracted with ethyl acetate, and then subjected to column chromatography through silica gel eluted with toluene, to give 7.6 g of 3,4-difluoro-N-ethyl-2-methoxy-N-(trifluoroacetyl)aniline (XII, R9' =ethyl) as a reddish-brown oil.

Workup

  1. distillationafter which the solvent was distilled off under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate
  3. washeluted with toluene

Sources & evidence

ORD record
ord-294d7833830f4af88a914142ccaf8085
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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