Benzoyl chloride → N-(4-fluoro-3-nitrophenyl)benzamide

HRID 605225Notes

Reaction equation

HRID 605225 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CCN(CC)CC.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 677684-Fluoro-3-nitroaniline

Product 1

HCID 3535228N-(4-fluoro-3-nitrophenyl)benzamideYield 81.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 4-fluoro-3-nitroaniline (2.00 g, 12.8 mmol) and Et3N (1.98 mL, 14.1 mmol) in THF (40 mL) was added benzoyl chloride (1.58 ml, 13.5 mmol) dropwise at 5° C. The mixture was stirred at 5° C. for 1 hour, warmed to room temperature, and then evaporated. The residue was suspended in H2O (100 ml), adjusted to pH 2, and then extracted with EtOAc. The extract was washed with H2O, 10% NaHCO3 and brine, dried over MgSO4, and concentrated under vacuum to give the crude product, which was purified by washing with i-Pr2O to give the title compound as pale brown crystal (2.70 g, 81%).

Workup

  1. temperaturewarmed to room temperature
  2. customevaporated
  3. extractionextracted with EtOAc
  4. washThe extract was washed with H2O, 10% NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum
  7. customto give the crude product, which
  8. customwas purified
  9. washby washing with i-Pr2O

Sources & evidence

ORD record
ord-fc9411b66fab42c6a4fae27770980d1c
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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