Acetanilide → 4'-Chloroacetyl(acetanilide)

HRID 840167

Reaction equation

HRID 840167 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[C:6]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])[CH3:7].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[Cl:1][CH2:2][C:3]([C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:6](=[O:8])[CH3:7])=[CH:11][CH:12]=1)=[O:4]

Participants

5

Reactant 3

HCID 904AcetanilideHCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 88054'-Chloroacetyl(acetanilide)

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

23.5 mmol of chloroacetyl chloride and, in portions, 18.1 mmol of acetanilide, are added slowly, under an argon atmosphere, to 108 mmol of aluminium chloride in 90 ml of 1,2-dichloroethane. The reaction mixture is heated at 60° C. for 2 hours and then cooled with an ice bath. After slow hydrolysis using ice, and filtration, the precipitate obtained is washed with ethyl ether and dried. The expected product so obtained is used in the following without being purified.

Workup

  1. temperaturecooled with an ice bath
  2. customAfter slow hydrolysis
  3. filtrationice, and filtration
  4. customthe precipitate obtained
  5. washis washed with ethyl ether
  6. customdried

Sources & evidence

ORD record
ord-8302ee1b619a44479dd5e646e1a4a518
Source dataset
uspto-grants-2002_04
Patent number
US06365605B1

Linked notes

Loading…