Chloroacetyl chloride → 2,4'-Dichloroacetanilide

HRID 2104407Notes

Reaction equation

HRID 2104407 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[Cl:9][CH2:10][C:11](Cl)=[O:12]>C(OCC)(=O)C>[Cl:9][CH2:10][C:11]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:12]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 78124-Chloroaniline

Product 1

HCID 949202,4'-Dichloroacetanilide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

p-Chloroaniline (3.82 g) was dissolved in ethyl acetate (30 mL), and, at room temperature, chloroacetyl chloride (2.39 mL) was added to the solution, followed by stirring for 1 hour. After the reaction mixture was heated and stirred at 60° C. for 3.5 hours, crystals precipitated were collected by filtration, to thereby give the title compound (4.78 g). The filtrate was concentrated to about ¼, and crystals precipitated were collected by filtration, to thereby give the title compound (1.01 g).

Workup

  1. temperatureAfter the reaction mixture was heated
  2. stirringstirred at 60° C. for 3.5 hours
  3. customcrystals precipitated
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-051a03cd9ce94746a625e0c96877df65
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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