3,4-Dichloroaniline → 2-(3,4-Dichloro-phenylamino)-propionic Acid ethyl ester

HRID 1096188Notes

Reaction equation

HRID 1096188 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].Br[CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O-])(O)=O.[Na+]>CCO>[CH2:15]([O:14][C:12](=[O:13])[CH:11]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([Cl:9])=[C:2]([Cl:1])[CH:3]=1)[CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 72573,4-DichloroanilineHCID 79040Ethyl 2-bromopropionate2×HCID 516892Sodium Bicarbonate2×

Product 1

HCID 69148082-(3,4-Dichloro-phenylamino)-propionic Acid ethyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3,4-dichloroaniline (20.0 g, 120 mmol), ethyl 2-bromopropionate (26.0 g, 144 mmoL), and NaHCO3 (15.1 g, 180 mmol) in EtOH (200 mL) was heated at reflux. After 16 h another portion of ethyl 2-bromopropionate (13.9 g, 96.7 mmol) and NaHCO3 (8.00 g, 95 mmol) was added, and the mixture heated at reflux for an additional 24 h, then evaporated under vacuum. The residue was partitioned between EtOAc and water. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane/EtOAc 1:1) afforded the title compound (26.1 g, 83%). Yellow oil, MS: 262.0 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperaturethe mixture heated
  4. temperatureat reflux for an additional 24 h
  5. customevaporated under vacuum
  6. customThe residue was partitioned between EtOAc and water
  7. washThe organic layer was washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-48e6597afac94b46bf20ccea89fe6835
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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