Methyl iodide → N-Boc 4-Iodo-N-methylaniline

HRID 412480Notes

Reaction equation

HRID 412480 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:18]I>CN(C)C=O>[C:1]([O:5][C:6]([N:8]([CH3:18])[C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2773612tert-butyl N-(4-iodophenyl)carbamate

Product 1

HCID 18537740N-Boc 4-Iodo-N-methylaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-tertiary-butyloxycarbonyl-4-iodoaniline (11.5 g, see P G Ciattini et al, Tet. Lett, 1995, 36, 4133-4136 for preparation) in dimethylformamide (70 mL), under nitrogen, was treated portionwise with sodium hydride (1.6 g, 60% dispersion in mineral oil). When effervescence had ceased (after about 5 minutes) the mixture was treated with methyl iodide and stirring was continued at room temperature for 2 hours. The reaction mixture was partitioned between ethyl acetate (500 mL) and water (500 mL). The organic phase was dried and then evaporated to give the title compound (11.5 g) as a pink oil.

Workup

  1. custom(after about 5 minutes)
  2. customThe reaction mixture was partitioned between ethyl acetate (500 mL) and water (500 mL)
  3. customThe organic phase was dried
  4. customevaporated

Sources & evidence

ORD record
ord-d3818de8d2f64178858115cfa92a3ce2
Source dataset
uspto-grants-2003_05
Patent number
US06562851B2

Reaction notes

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