Water → Benzamide, N-(4-fluoro-3-nitrophenyl)-N-methyl-

HRID 722409

Reaction equation

HRID 722409 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].I[CH3:21].[H-].[Na+].O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:21])[C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3535228N-(4-fluoro-3-nitrophenyl)benzamide

Product 1

HCID 11460004Benzamide, N-(4-fluoro-3-nitrophenyl)-N-methyl-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(4-fluoro-3-nitro-phenyl)-benzamide (1.60 g, 6.15 mmol) in anhydrous DMF was added iodomethane (3.49 g, 24.60 mmol, 1.53 ml) under argon. 60% Sodium hydride (0.37 g, 9.23 mmol) was then added portionwise to the cooled solution (0° C.) and the reaction mixture was then stirred at room temperature for 24 h. The solution was poured slowly into water and the aqueous layer was extracted 3× with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The residue was purified by flash chromatography, eluting with hexane/ethyl acetate (4:1) to give N-(4-fluoro-3-nitro-phenyl)-N-methyl-benzamide. (1.47 g, 87%)

Workup

  1. extractionthe aqueous layer was extracted 3× with ethyl acetate
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by flash chromatography
  5. washeluting with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-e80efaf38bfa4c289894f176ae48ca8d
Source dataset
uspto-grants-2006_11
Patent number
US07138420B2

Linked notes

Loading…