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

HRID 2233226Notes

Reaction equation

HRID 2233226 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(N(CC)CC)C.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[C:19]([NH:4][C:3]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:2]=1[CH3:1])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 74412-Methyl-4-nitroanilineHCID 8471Triethylamine

Product 1

HCID 2835288N-(2-methyl-4-nitrophenyl)benzamideYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-methyl-4-nitroaniline (2.03 g, 13.3 mmol), triethylamine (2.00 ml, 14.6 mmol) and benzoyl chloride (1.70 ml, 14.6 mmol) were heated in toluene (50 ml) at reflux for 2 hours under an inert atmosphere. The reaction was allowed to cool to ambient temperature overnight, causing precipitation of a white solid. The solid was collected by suction filtration, washed with toluene (3×50 ml), dissolved in dichloromethane (100 ml) and washed with water (3×50 ml). Drying of the organic layer over magnesium sulphate, followed by solvent evaporation in vacuo, yielded N-benzoyl 2-methyl-4-nitroaniline (3.06 g, 90% yield) as a white solid:

Workup

  1. temperatureat reflux for 2 hours under an inert atmosphere
  2. customprecipitation of a white solid
  3. filtrationThe solid was collected by suction filtration
  4. washwashed with toluene (3×50 ml)
  5. dissolutiondissolved in dichloromethane (100 ml)
  6. washwashed with water (3×50 ml)
  7. dry with materialDrying of the organic layer over magnesium sulphate
  8. customfollowed by solvent evaporation in vacuo

Sources & evidence

ORD record
ord-ce9ccba54c3c4225a85ad85786b943bb
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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