Potassium Carbonate → 1-(4-Chloro-2-phenylaminophenyl)ethanone

HRID 1697058Notes

Reaction equation

HRID 1697058 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].C([O-])([O-])=O.[K+].[K+].I[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(OCCCC)CCC.[Cu]>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([C:9](=[O:11])[CH3:10])=[C:2]([NH:1][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium Carbonate2×HCID 11575Iodobenzene2×HCID 135747171-(2-Amino-4-chlorophenyl)ethanone

Product 1

HCID 598461761-(4-Chloro-2-phenylaminophenyl)ethanone

Reagents, catalysts & solvents 2

HCID 23978CopperCatalyst2×HCID 8909Butyl etherSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1-(2-amino-4-chlorophenyl)-ethanone (1.85 g), copper powder (140 mg), KI (360 mg), K2CO3 (3.06 g) and iodobenzene (4.8 mL) in dibutyl ether (40 mL) was heated at 160° C. (oil bath temperature) overnight. More copper powder (140 mg), KI (360 mg), K2CO3 (3.06 g) and iodobenzene (4.8 mL) were added and the reaction mixture was heated at reflux overnight. The resulting mixture was then cooled and concentrated under reduced pressure. The residue was partitioned between water and ethyl acetate, the organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexane) to afford 2.2 g of 1-(4-chloro-2-phenylamino-phenyl)-ethanone.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux overnight
  3. temperatureThe resulting mixture was then cooled
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between water and ethyl acetate
  6. customthe organic layer was separated
  7. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customevaporated under reduced pressure
  12. customThe crude residue was purified by flash chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-6a225bacc6b649498a96655b2858c887
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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