2-Nitroaniline → Benzamide, 4-nitro-N-(2-nitrophenyl)-

HRID 441227Notes

Reaction equation

HRID 441227 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].C(N(CC)CC)C.[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)([O-:20])=[O:19]>ClCCl>[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][C:25](=[O:26])[C:24]1[CH:23]=[CH:22][C:21]([N+:18]([O-:20])=[O:19])=[CH:29][CH:28]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 69462-NitroanilineHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chloride

Product 1

HCID 5155676Benzamide, 4-nitro-N-(2-nitrophenyl)-Yield 63.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-nitroaniline (1.38 g) and triethylamine (1.67 ml) in dichloromethane (30 ml) were added 4-nitrobenzoyl chloride (1.85 g) and the solution was stirred at ambient temperature for 4 hours. The solution was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate, water and brine, and the organic layer was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was solidified with n-hexane to give 2-nitro-N-(4nitrobenzoyl)aniline (1.82 g).

Workup

  1. washThe solution was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate, water and brine
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-884c8b27e2124b9c80f5c99e079dfec6
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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