Water → Ethyl 2-((3-(benzyloxy)phenyl)amino)acetate

HRID 709641Notes

Reaction equation

HRID 709641 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:12][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 928923-BenzyloxyanilineHCID 517045Sodium Acetate

Product 1

HCID 117760232Ethyl 2-((3-(benzyloxy)phenyl)amino)acetateYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(benzyloxy)aniline (5.00 g) in DMF (50% mL) were added sodium acetate (2.10 g) and ethyl bromoacetate (4.20 g), and the mixture was stirred at room temperature for 12 hr. Water was added, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.80 g) as orange crystals.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-84ca6ea35b884cafa060a241142cab1c
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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