Diethyl Ether → N-(2-fluoro-5-nitrophenyl)benzamide

HRID 1357692

Reaction equation

HRID 1357692 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:10]=1[NH2:11].[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(OCC)C>C(Cl)Cl>[CH3:23][CH2:22][CH2:21][CH:20]([CH3:25])[CH3:19].[F:8][C:9]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:10]=1[NH:11][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 677852-Fluoro-5-nitroaniline

Product 2

HCID 78922-MethylpentaneHCID 675819N-(2-fluoro-5-nitrophenyl)benzamideYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (5.85 ml) was added to a an ice-cooled solution of 2-fluoro-5-nitroaniline (3.9 g) in dry methylene chloride under an argon atmosphere. Benzoyl chloride (4.18 ml) was added gradually. The resulting mixture was stirred at ambient temperature for 18 hours. The reaction mixture was partitioned between water and methylene chloride, the organic phase was washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulphate, filtered and evaporated to dryness to give a sticky solid. Trituration with hot isohexane and diethyl ether gave N-(2-fluoro-5-nitrophenyl)benzamide as a solid (3.2 g, 49%); NMR (CDCl3) 7.26 (dd, 1H), 7.6 (m, 3H), 7.91 (d, 2H), 8.03 (m, 1H), 8.15 (broad s, 1H), 9.48 (dd, 1H); m/s: M+H+ 261.

Workup

  1. customThe reaction mixture was partitioned between water and methylene chloride
  2. washthe organic phase was washed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto give a sticky solid

Sources & evidence

ORD record
ord-49c602cd1d9e4506b980a12d6d37334b
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Linked notes

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