Benzoyl chloride → Benzamide, N-(5-chloro-2-hydroxy-4-nitrophenyl)-

HRID 1904885Notes

Reaction equation

HRID 1904885 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OCC)(=O)C>[C:13]([NH:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 38948482-Amino-4-chloro-5-nitrophenol

Product 1

HCID 5483228Benzamide, N-(5-chloro-2-hydroxy-4-nitrophenyl)-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In 100 ml of ethyl acetate was dissolved 40 g (210×10-3 mole) of 2-amino-4-chloro-5-nitrophenol, and 33 g of benzoyl chloride was added at room temperature and then the mixture was refluxed under heating for 2 hours. After the reaction, a solvent was distilled off under reduced pressure and the residue was recrystallized from hexane to obtain products. Yield: 60 g.

Workup

  1. additionwas added at room temperature
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 2 hours
  4. customAfter the reaction
  5. distillationa solvent was distilled off under reduced pressure
  6. customthe residue was recrystallized from hexane
  7. customto obtain products

Sources & evidence

ORD record
ord-2e06502417ee40d693de4722bb29c439
Source dataset
uspto-grants-1989_06
Patent number
US04840883

Reaction notes

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