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

HRID 1859662Notes

Reaction equation

HRID 1859662 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].C(N(CC)CC)C>C(OCC)(=O)C>[N+:18]([C:12]1[CH:13]=[C:14]([NH:15][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:16]=[CH:17][C:11]=1[F:10])([O-:20])=[O:19]

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 8857Ethyl AcetateSolvent

Procedure

Benzoyl chloride (12 mL, 103 mmol) was added dropwise to 4-fluoro-3-nitroaniline (15.64 g, 100 mmol) and triethylamine (17 mL, 122 mmol) in ethyl acetate (400 mL) at room temperature. The reaction mixture was stirred for 2 hours and then allowed to stand overnight. The reaction mixture was washed with 10% aqueous citric acid solution (200 mL), saturated aqueous sodium bicarbonate solution (200 mL), and brine (100 mL); dried (magnesium sulfate), filtered, and concentrated to about 100 mL at which point a solid began to precipitate. The mixture was cooled to zero degrees and the straw-colored solid collected by filtration to afford the product (21.1 g) in two crops.

Workup

  1. waitto stand overnight
  2. washThe reaction mixture was washed with 10% aqueous citric acid solution (200 mL), saturated aqueous sodium bicarbonate solution (200 mL), and brine (100 mL)
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated to about 100 mL at which point a solid
  6. customto precipitate
  7. temperatureThe mixture was cooled to zero degrees
  8. filtrationthe straw-colored solid collected by filtration

Sources & evidence

ORD record
ord-c1c66a8fa2f143b3909ca2848490ee33
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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