Phenylacetyl chloride → N-(5-chloro-2-methyl-4-nitrophenyl)-2-phenylacetamide

HRID 605288Notes

Reaction equation

HRID 605288 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]1([CH2:19][C:20](Cl)=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=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:20](=[O:21])[CH2:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 7679Phenylacetyl chlorideHCID 837726-Chloro-4-nitro-o-toluidine

Product 1

HCID 2907847N-(5-chloro-2-methyl-4-nitrophenyl)-2-phenylacetamideYield 43%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-chloro-2-methyl-4-nitrophenylamine (0.475 g, 2.55 mmol) and phenylacetyl chloride (0.394 g, 2.55 mmol) in toluene (10 mL) was heated under reflux for 4 h, then 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 yellow solid (0.330 g, 43%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 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-7ed94397d16a41d691a3c66a4becd791
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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