Water → 2-(4-bromo-phenyl)-N-ethyl-propionamide

HRID 409719Notes

Reaction equation

HRID 409719 reaction equation
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=O)=[CH:10][CH:9]=1.Cl.[CH2:20]([NH2:22])[CH3:21].O>C(Cl)Cl>[CH2:20]([NH:22][C:15](=[O:17])[CH:14]([C:11]1[CH:10]=[CH:9][C:8]([Br:7])=[CH:13][CH:12]=1)[CH3:18])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 11198Ethylamine hydrochlorideHCID 65578Oxalyl chlorideHCID 5214412-(4-Bromophenyl)propanoic acid

Product 1

HCID 866861072-(4-bromo-phenyl)-N-ethyl-propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

16.6 g (130 mmol) oxalyl chloride are added to 15.0 g (65 mmol) 2-(4-bromo-phenyl)-propionic acid (Bioorg. Med. Chem. Lett. 2010, 20, 887) in 75 mL DCM at 0° C. The cooling is removed and the mixture is stirred for 2 h under reflux. After that time, the solvent is evaporated and the residue is taken up in 70 mL THF. 3.20 g (39 mmol) ethylamine hydrochloride and 66.0 g (655 mmol) TEA are added and the mixture is stirred for 16 h at rt. After that time, iced water is added, the mixture is extracted with EtOAc and the organic layer is dried over sodium sulphate. The solvent is evaporated and the residue is purified by column chromatography (silica gel).

Workup

  1. customThe cooling is removed
  2. temperatureunder reflux
  3. customAfter that time, the solvent is evaporated
  4. stirringthe mixture is stirred for 16 h at rt
  5. extractionthe mixture is extracted with EtOAc
  6. dry with materialthe organic layer is dried over sodium sulphate
  7. customThe solvent is evaporated
  8. customthe residue is purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-620f16dbe10d40d2a6b9c408f3cf1101
Source dataset
uspto-grants-2014_06
Patent number
US08759528B2

Reaction notes

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