Potassium Iodide → HCID 22258810, compound

HRID 412225Notes

Reaction equation

HRID 412225 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:3]=1[C:4]([N:6]([O:8][CH3:9])[CH3:7])=[O:5].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[F:1][C:2]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:21][C:20]2[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)[C:3]=1[C:4]([N:6]([O:8][CH3:9])[CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 22258717HCID 22258717, compound

Product 1

HCID 22258810HCID 22258810, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 2-fluoro-6-hydroxy-N-methoxy-N-methylbenzamide (4.320 g, 21.689 mmol) in acetone (50 mL) were added 4-methoxy benzylchloride (3.74 g, 23.858 mmol), potassium carbonate (4.50 g, 32.534 mmol), and potassium iodide (360 mg, 2.169 mmol). The mixture was stirred at reflux for 15 hrs. After cooled to room temperature, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was extracted with ethyl acetate and water. The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give 2-fluoro-N-methoxy-6-[(4-methoxybenzyl)oxy]-N-methylbenzamide as a pale yellow oil (6.926 g, yield; quant.).

Workup

  1. temperatureat reflux for 15 hrs
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate and water
  5. washThe separated organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1)
  10. customto give

Sources & evidence

ORD record
ord-aa21eb736e044e09a2a939e24cf67826
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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