Reaction #75457

ord-9f09deab17364e32ae4c5faddf67d636

Reaction equation

O=C(Cl)c1ccc(Cl)c(Cl)c1
3,4-dichlorobenzoyl chloride
Nc1cc(Cl)c([N+](=O)[O-])cc1O
2-amino-4-chloro-5-nitrophenol
O=C(Nc1cc(Cl)c([N+](=O)[O-])cc1O)c1ccc(Cl)c(Cl)c1
2-(3,4-dichlorobenzamido)-4-chloro-5-nitrophenol
Yield 77.0%

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturethe mixture refluxed for 2 h
  2. 2
    TemperatureAfter cooling the precipitate
  3. 3
    Filtrationwas filtered
  4. 4
    Filtrationfiltered again

Procedure

3,4-dichlorobenzoyl chloride (2) (38.0 g, 0.18 mol) was added to a stirred slurry of 2-amino-4-chloro-5-nitrophenol (1) (34.0 g, 0.18 mol) in ethyl acetate (250 ml) and the mixture refluxed for 2 h. After cooling the precipitate was filtered and then slurried in hot ethyl acetate (200 ml) and filtered again to give 50 g (77%) 2-(3,4-dichlorobenzamido)-4-chloro-5-nitrophenol (3).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06699650B1uspto-grants-2004_03