Ethyl bromoacetate → Ethyl 2-(4,5-dichloro-2-ethylphenylamino)acetate

HRID 588784Notes

Reaction equation

HRID 588784 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([CH2:10][CH3:11])[CH:3]=1.[H-].[Na+].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C=O)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:4]([CH2:10][CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 213368484,5-Dichloro-2-ethylbenzenamine

Product 1

HCID 117610674Ethyl 2-(4,5-dichloro-2-ethylphenylamino)acetateYield 44.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 4,5-dichloro-2-ethylbenzenamine (600 mg, 3.15 mmol) in DMF at 0° C., NaH (150 mg, 3.78 mmol) was added in portions. After stirring for 30 min, ethyl 2-bromoacetate (789 mg, 4.74 mmol) was added to the mixture. The resulting mixture was stirred at 120° C. for 16 h. The mixture was allowed to cool to room temperature, poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=5:1) to afford the desired product (380 mg, 44.7% yield) as a yellow solid.

Workup

  1. stirringThe resulting mixture was stirred at 120° C. for 16 h
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-0fed17fce140469bbc32c701a81c0810
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

Loading…