Chloroacetyl chloride → 2,4'-Dichloroacetanilide

HRID 902880

Reaction equation

HRID 902880 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 chloroacetyl chloride (2.39 ml) was added at room temperature to stir the mixture for 1 hour. After the reaction mixture was heated and stirred at 60° C. for 3.5 hours, crystals deposited were collected by filtration to obtain the title compound (4.78 g). The filtrate was concentrated to about 1/4, and crystals deposited were collected by filtration to obtain the title compound (1.01 g).

Workup

  1. temperatureAfter the reaction mixture was heated
  2. stirringstirred at 60° C. for 3.5 hours
  3. filtrationcrystals deposited were collected by filtration

Sources & evidence

ORD record
ord-b3e2a0c965c64eceb565008c59d758a2
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Linked notes

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