Water → 2'-Nitrobenzanilide

HRID 987204Notes

Reaction equation

HRID 987204 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8])([O-:5])=[O:4].[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>O1CCCC1>[C:13]([NH:8][C:7]1[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=1[N+:3]([O-:5])=[O:4])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 69462-NitroanilineHCID 7412Benzoyl chlorideHCID 24758Sodium hydride

Product 1

HCID 697692'-Nitrobenzanilide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.58 g of sodium hydride (60% content) was suspended in 19.80 g of tetrahydrofuran and cooled with ice. To the obtained suspension, 19.83 g of a tetrahydrofuran solution containing 2.50 g of 2-nitroaniline was dropwise added over 1 hour, stirred for 10 minutes, allowed to stand at room temperature and stirred for 30 minutes. To the obtained mixture, 2.77 g of benzoyl chloride was added dropwise over 0.5 hr at room temperature and stirred for 2 hours. The reaction mixture was added to water and separated. The separated organic layer was washed with sodium hydroxide solution and saline to obtain an organic layer, which was analyzed by high performance liquid chromatography to find the yield of the desired product was 82%.

Workup

  1. temperaturecooled with ice
  2. additionwas dropwise added over 1 hour
  3. customto stand at room temperature
  4. stirringstirred for 30 minutes
  5. stirringstirred for 2 hours
  6. customseparated
  7. washThe separated organic layer was washed with sodium hydroxide solution and saline
  8. customto obtain an organic layer, which

Sources & evidence

ORD record
ord-1092eb530ff34927945f1dc89734a848
Source dataset
uspto-grants-2003_10
Patent number
US06630598B2

Reaction notes

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