Water → 2-chloro-N-(2-formylphenyl)acetamide

HRID 228842Notes

Reaction equation

HRID 228842 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Cl:10][CH2:11][C:12](Cl)=[O:13].O>ClCCl>[Cl:10][CH2:11][C:12]([NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 682552-Aminobenzaldehyde

Product 1

HCID 125333492-chloro-N-(2-formylphenyl)acetamideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Aminobenzaldehyde (650 mg) was dissolved in dichloromethane (20 ml) to prepare a solution. Chloroacetyl chloride (728 mg) was added to the solution, and the mixture was stirred at room temperature overnight. Water was added thereto, and the mixture was extracted with dichloromethane. The dichloromethane layer was washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using chloroform to give 2-chloro-N-(2-formylphenyl)-acetamide (1.05 g, yield 99%).

Workup

  1. customto prepare a solution
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe dichloromethane layer was washed with water and saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7253859b6f0a4d0b8d00265a83cf1321
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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