Benzoyl chloride → N-(5-chloro-2-methyl-4-nitrophenyl)benzamide

HRID 605292Notes

Reaction equation

HRID 605292 reaction equation
[Cl:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[CH:4][C:5]([CH3:9])=[C:6]([NH2:8])[CH:7]=1.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[CH:4][C:5]([CH3:9])=[C:6]([NH:8][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 837726-Chloro-4-nitro-o-toluidine

Product 1

HCID 4158578N-(5-chloro-2-methyl-4-nitrophenyl)benzamideYield 32%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-chloro-2-methyl-4-nitrophenylamine (0.560 g, 3.00 mmol) and benzoyl chloride (0.422 g, 3.00 mmol) in toluene (15 mL) was heated under reflux for 1.5 h, and cooled to room temperature. A solid crystallized from the reaction mixture upon cooling, and was isolated by vacuum filtration and dried to provide the title compound as a gray solid (0.276 g, 32%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 h
  3. customA solid crystallized from the reaction mixture
  4. temperatureupon cooling
  5. customwas isolated by vacuum filtration
  6. customdried

Sources & evidence

ORD record
ord-ddf67a31fca7406ab29e0738bd32721d
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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