Methyl iodide → HCID 14856787, compound

HRID 1110804Notes

Reaction equation

HRID 1110804 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]=[O:12])=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=1.[CH3:16]I>CN(C)C=O>[CH3:16][N:10]([C:7]1[CH:8]=[CH:9][C:4]([CH3:3])=[CH:5][C:6]=1[N+:13]([O-:15])=[O:14])[CH:11]=[O:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 345693771894-91-2

Product 1

HCID 14856787HCID 14856787, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
50 °C

Procedure

In an argon flow, 8.1 g (202 mmols) of sodium hydride (60% in oil) was added to 400 ml of dry dimethylformamide and the mixture was cooled to 5° to 10° C. To the mixture was dropwise added 34.7 g (192 mmols) of N-(4-methyl -2nitrophenyl)formamide (a solution in 150 ml of dry dimethylformamide). The mixture was stirred at 50° C. for an hour. After cooling again to 5° to 10° C., 18 ml (289 mmols) of methyl iodide (a solution in 30 ml of dry dimethylformamide) was dropwise added to the mixture. The system was stirred at room temperature for 16 hours. After the solvent was distilled off under reduced pressure, 200 ml of water was added to the residue followed by extraction with ethyl acetate. After the ethyl acetate layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting crystals were washed with n-hexane to give 31.2 g (83.4%) of N-methyl-N-(4-methyl2-nitrophenyl)formamide.

Workup

  1. temperaturethe mixture was cooled to 5° to 10° C
  2. temperatureAfter cooling again to 5° to 10° C.
  3. stirringThe system was stirred at room temperature for 16 hours
  4. distillationAfter the solvent was distilled off under reduced pressure, 200 ml of water
  5. additionwas added to the residue
  6. extractionfollowed by extraction with ethyl acetate
  7. washAfter the ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. washThe resulting crystals were washed with n-hexane

Sources & evidence

ORD record
ord-327fca5ea2ca40be840c7e76f08facfa
Source dataset
uspto-grants-1990_12
Patent number
US04977175

Reaction notes

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