Water → tert-butyl N-(3-benzyloxy-2-nitrophenyl)-N-ethylcarbamate

HRID 636468Notes

Reaction equation

HRID 636468 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N+:23]([O-:25])=[O:24])=[C:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:28](I)[CH3:29].O>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:10]([N+:23]([O-:25])=[O:24])=[C:11]([N:15]([CH2:28][CH3:29])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 10783643tert-butyl N-(3-benzyloxy-2-nitrophenyl)carbamate

Product 1

HCID 10666991tert-butyl N-(3-benzyloxy-2-nitrophenyl)-N-ethylcarbamateYield 103.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl N-(3-benzyloxy-2-nitrophenyl)carbamate (3 g) in dimethylformamide (30 ml) was added sodium hydride (60% in oil, 575 mg) under ice-cooling, and the mixture was stirred for 15 minutes. To the mixture was added ethyl iodide (1.49 g), and the mixture was stirred for 2 hours at ambient temperature. To the reaction mixture was added water (150 ml), and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1, v/v) and crystallized with hexane to give tert-butyl N-(3-benzyloxy-2-nitrophenyl)-N-ethylcarbamate (3.36 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 2 hours at ambient temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane
  8. customethyl acetate=5:1, v/v) and crystallized with hexane

Sources & evidence

ORD record
ord-906e14cc26e24f338993e9f81422814b
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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