Methyl iodide → HCID 22010661, compound

HRID 323128Notes

Reaction equation

HRID 323128 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[NH:16][C:17](=[O:27])[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:31]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[N:16]([CH3:31])[C:17](=[O:27])[C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22010922HCID 22010922, compound

Product 1

HCID 22010661HCID 22010661, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(2-benzyloxy-4-methylphenyl)-4-nitrobenzamide (4.7 g) in N,N-dimethylformamide (50 ml) was treated with sodium hydride (623 mg, 60% w/w in mineral oil) at 0° C. After 30 minutes, iodomethane (1.21 ml) was added, and the reaction mixture was stirred for 3 hours. The reaction was quenched with water and the mixture diluted with ethyl acetate. The organic phase was washed with water and brine. The organic solution was dried over magnesium sulfate and concentrated to give N-(2-benzyloxy-4-methylphenyl)-N-methyl-4-nitrobenzamide (4.6 g).

Workup

  1. customThe reaction was quenched with water
  2. additionthe mixture diluted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialThe organic solution was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1718ad30613a46f2aaa79dd808007947
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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