Methyl iodide → N-(3-bromo-5-nitrophenyl)-N-methylacetamide

HRID 1603614Notes

Reaction equation

HRID 1603614 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[H-].[Na+].[CH3:17]I>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([N:11]([CH3:17])[C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10658908N-(3-bromo-5-nitrophenyl)acetamide

Product 1

HCID 10683645N-(3-bromo-5-nitrophenyl)-N-methylacetamideYield 88.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

31.0 g (0.1197 mol) of N-(3-bromo-5-nitrophenyl)-acetamide were dissolved in 240 ml of dimethylformamide and added dropwise within 20 min. to a suspension, cooled at 5° C., of 5.8 g (0.1325 mol) of NaH (60%) in 120 ml of dimethylformamide. Subsequently, the mixture was stirred at room temperature for 1 hr., again cooled to 0-5° C. and 22.30 ml (0.358 mol) of MeI were added thereto. The mixture was stirred at room temperature for 18 hrs., then freed from solvent and the residue was partitioned in water and dichloromethane. The organic phase was washed with sat. sodium chloride solution, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane. There were obtained 29.0 g (88.7%) of N-(3-bromo-5-nitrophenyl)-N-methylacetamide as a brown oil. MS (El): me/e=274,272 (C9H9BrN2O3+).

Workup

  1. additionadded dropwise within 20 min. to a suspension
  2. temperature, again cooled to 0-5° C.
  3. stirringThe mixture was stirred at room temperature for 18 hrs
  4. customthe residue was partitioned in water
  5. washThe organic phase was washed with sat. sodium chloride solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was chromatographed on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-448bf9f84eec447b8453a0028f811875
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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