tert-butyl N-(3-benzyloxy-2-nitrophenyl)-N-ethylcarbamate → HCID 10707324, compound

HRID 636469Notes

Reaction equation

HRID 636469 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N+:25]([O-:27])=[O:26])=[C:11]([N:15]([CH2:23][CH3:24])C(=O)OC(C)(C)C)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.Cl>>[CH2:1]([O:8][C:9]1[C:10]([N+:25]([O-:27])=[O:26])=[C:11]([CH:12]=[CH:13][CH:14]=1)[NH:15][CH2:23][CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 10666991tert-butyl N-(3-benzyloxy-2-nitrophenyl)-N-ethylcarbamateHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 10707324HCID 10707324, compoundYield 94.9%

Procedure

To tert-butyl N-(3-benzyloxy-2-nitrophenyl)-N-ethylcarbamate (3.30 g) was added 4N hydrogen chloride—ethyl acetate solution (15 ml) under ice-cooling, and the mixture was stirred for 10 minutes at the same temperature and then for 30 minutes at ambient temperature. The solvent was removed in vacuo, saturated sodium bicarbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo to give 3-benzyloxy-N-ethyl-2-nitroaniline (2.29 g).

Workup

  1. temperaturecooling
  2. waitfor 30 minutes at ambient temperature
  3. customThe solvent was removed in vacuo, saturated sodium bicarbonate solution
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-3ad47977b0c94418a2dc5cadd7f60cf2
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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