1-Chloro-4-nitrobenzene → N-(4-Chlorophenyl)acetamide

HRID 347398Notes

Reaction equation

HRID 347398 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][CH:3]=1.[C:11]([OH:14])(=S)[CH3:12]>C([O-])([O-])=O.[K+].[K+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:11](=[O:14])[CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 74741-Chloro-4-nitrobenzeneHCID 178418634HCID 178418634, compound

Product 1

HCID 10871N-(4-Chlorophenyl)acetamideYield 91%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateCatalyst

Conditions

Temperature
150 °C

Procedure

In one example, under nitrogen gas, a stirred mixture of 4-Chloro-1-nitrobenzene (e.g., about 1 g, 6.35 mmol), thioacetic acid (e.g., about 1.93 g, 25.39 mmol), K2CO3 (e.g., about 0.050 g, 0.36 mmol), and dry Triton-X 405 (e.g., about 0.010 g) were heated at about 150° C. The progress of the reaction was monitored by HPLC and GC. After four hours the reaction was cooled to room temperature, and acetone (e.g., about 8 mL) was added and filtered through a sintered glass funnel. Evaporation of the acetone produced about 0.975 g of N-(4-Chloro-phenyl)-acetamide (e.g., about 91%).

Workup

  1. customdry Triton-X 405 (e.g., about 0.010 g)
  2. temperatureAfter four hours the reaction was cooled to room temperature
  3. additionacetone (e.g., about 8 mL) was added
  4. filtrationfiltered through a sintered glass funnel
  5. customEvaporation of the acetone

Sources & evidence

ORD record
ord-61da0582113a45c69fa1cfe0f8661d35
Source dataset
uspto-grants-2007_02
Patent number
US07173152B2

Reaction notes

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