Methyl iodide → N-(4-fluoro-3-nitrophenyl)-N-methylacetamide

HRID 1987201Notes

Reaction equation

HRID 1987201 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[CH:6][C:5]=1[N+:14]([O-:16])=[O:15].I[CH3:18]>C1COCC1>[F:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH3:18])[C:11](=[O:13])[CH3:12])=[CH:6][C:5]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67694Acetamide, N-(4-fluoro-3-nitrophenyl)-

Product 1

HCID 57441080N-(4-fluoro-3-nitrophenyl)-N-methylacetamideYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (4.22 g, 60%, 106 mmol) was added portionwise to a solution of N-(4-fluoro-3-nitrophenyl)acetamide (13.9 g, 70 mmol) in THF (200 mL) at 0° C. Stirring for 20 min, iodomethane (18.5 g, 130 mmol) was added. The reaction mixture was stirred at room temperature for 2 h, quenched with saturated NaHCO3 (30 mL) and extracted with EtOAc (3×100 mL). The combined organic phases were washed with saturated NaCl (2×50 mL). After filtration and concentration, 13.1 g (88%) of the title compound was obtained as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-D): δ 1.92 (s, 3 H), 3.30 (s, 3 H), 7.38 (s, 1 H), 7.52 (s, 1 H), 7.95 (s, 1 H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 h
  2. customquenched with saturated NaHCO3 (30 mL)
  3. extractionextracted with EtOAc (3×100 mL)
  4. washThe combined organic phases were washed with saturated NaCl (2×50 mL)
  5. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-a3ce5d2a59744b069f0495b36abb8d34
Source dataset
uspto-grants-2009_06
Patent number
US07550495B2

Reaction notes

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