Benzoyl chloride → N-(2-methyl-4-nitrophenyl)benzamide

HRID 38146

Reaction equation

HRID 38146 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH:4][C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 74412-Methyl-4-nitroaniline

Product 1

HCID 2835288N-(2-methyl-4-nitrophenyl)benzamideYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 2-methyl-4-nitroaniline (0.76 g, 5 mmol) in toluene (25 mL) was added neat benzoyl chloride (0.59 mL, 5.08 mmol). The reaction mixture was refluxed for 16 hr, cooled and filtered to give N-(2-methyl-4-nitrophenyl)benzamide (1.21 g, 95%) as a beige solid. ES-MS (M+H)+=257.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hr
  2. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-cfb21d133e044f9098f617d99185e3d2
Source dataset
uspto-grants-2013_09
Patent number
US08524721B2

Linked notes

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