Benzoyl chloride, 3,4-dichloro- → 3,4-Dichloro-N-(5-chloro-2-hydroxy-4-nitrophenyl)benzamide

HRID 47179

Reaction equation

HRID 47179 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](Cl)=[O:6].[NH2:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][C:14]=1[OH:23]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([NH:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][C:14]=1[OH:23])=[O:6]

Participants

4

Reactant 2

HCID 76403Benzoyl chloride, 3,4-dichloro-HCID 38948482-Amino-4-chloro-5-nitrophenol

Product 1

HCID 120977653,4-Dichloro-N-(5-chloro-2-hydroxy-4-nitrophenyl)benzamideYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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).

Workup

  1. temperaturethe mixture refluxed for 2 h
  2. temperatureAfter cooling the precipitate
  3. filtrationwas filtered
  4. filtrationfiltered again

Sources & evidence

ORD record
ord-9f09deab17364e32ae4c5faddf67d636
Source dataset
uspto-grants-2004_03
Patent number
US06699650B1

Linked notes

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