Diethyl Ether → N-Methyl-4-nitro-N-phenylbenzamide

HRID 323123Notes

Reaction equation

HRID 323123 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)([O-:18])=[O:17].C(OCC)C>ClCCl>[CH3:1][N:2]([C:23](=[O:24])[C:22]1[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:27][CH:26]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7515N-MethylanilineHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chloride

Product 1

HCID 265160N-Methyl-4-nitro-N-phenylbenzamideYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice bath cooled solution of N-methylaniline (536 mg) in dichloromethane (30 ml) were added triethylamine (0.837 ml) and p-nitrobenzoyl chloride (982 mg) and the mixture was stirred at ambient temperature for 3 hours. The solution was washed successively in 1N hydrogen chloride, saturated aqueous sodium hydrogen carbonate solution and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo to give an oil and the oil was solidified with diethyl ether to give N-methyl-N-(4-nitrobenzoyl)aniline (1.11 g) as a pale yellow solid.

Workup

  1. washThe solution was washed successively in 1N hydrogen chloride
  2. dry with materialsaturated aqueous sodium hydrogen carbonate solution and brine, and dried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customto give an oil

Sources & evidence

ORD record
ord-2a32cbed84664722b9366fa28754da6e
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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