Methyl iodide → (4-Benzyloxy-phenyl)-methyl-(4-methyl-2-nitro-phenyl)-amine

HRID 607244Notes

Reaction equation

HRID 607244 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=2[N+:23]([O-:25])=[O:24])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28]I>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]([CH3:28])[C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=2[N+:23]([O-:25])=[O:24])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66808397(4-Benzyloxy-phenyl)-(4-methyl-2-nitro-phenyl)-amine

Product 1

HCID 66808474(4-Benzyloxy-phenyl)-methyl-(4-methyl-2-nitro-phenyl)-amineYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of the product from Example 133A (229.4 mg, 0.6861 mmol) in anhydrous N,N-dimethylformamide (3 mL) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 55 mg, 1.372 mmol) in N,N-dimethylformamide (3 mL) at room temperature under a nitrogen atmosphere. The reaction was stirred at room temperature for 1 hour, then added methyl iodide (0.171 mL, 2.744 mmol) and let stir at room temperature for 2 hours. The solvent was removed by rotary evaporation under vacuum. The residue was taken up in water (30 mL) and extracted with methylene chloride (50 mL). The organic phase was washed with water (30 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated by rotary evaporation under vacuum to afford the title compound as a maroon-colored solid (239 mg, 100%).

Workup

  1. customThe solvent was removed by rotary evaporation under vacuum
  2. extractionextracted with methylene chloride (50 mL)
  3. washThe organic phase was washed with water (30 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation under vacuum

Sources & evidence

ORD record
ord-794fcf4829aa455f9e2f5110d0b9177e
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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