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

HRID 1261752Notes

Reaction equation

HRID 1261752 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 11575IodobenzeneHCID 135747171-(2-Amino-4-chlorophenyl)ethanone

Product 1

HCID 598461761-(4-Chloro-2-phenylaminophenyl)ethanoneYield 67.6%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalyst2×HCID 8909Butyl etherSolvent

Conditions

Temperature
142.5 °C

Procedure

A 3-necked round-bottomed flask equipped with a mechanic stirrer, a thermocouple probe, a reflux condenser and a nitrogen bubbler was charged with 1-(2-amino-4-chlorophenyl)ethanone (81 g, 478 mmol) in di-n-butyl ether (1 L). The reaction was then treated with pulverized potassium carbonate (200 g, 1.45 mol) and copper powder (5 g, 78 mmol). The reaction mixture was refluxed at 140-145° C. for 3 h. At this time, additional potassium carbonate (100 g, 0.72 mol), iodobenzene (100 g, 0.49 mol) and copper powder (2 g, 31 mmol) was added. The resulting mixture was refluxed overnight. At this time, the reaction was cooled to 25° C., filtered and washed with methyl tert-butyl ether. The filtrate was concentrated in vacuo. Flash chromatography (4″×16″ silica gel column; 0-2% ethyl acetate/hexanes) followed by concentration of the appropriate fractions, slurrying with hexanes, filtration and drying afforded 1-(4-chloro-2-phenylamino-phenyl)-ethanone (79.3 g, 67.6%) as a yellow solid. This material was used without further purification.

Workup

  1. customA 3-necked round-bottomed flask equipped with a mechanic stirrer
  2. temperatureThe resulting mixture was refluxed overnight
  3. temperatureAt this time, the reaction was cooled to 25° C.
  4. filtrationfiltered
  5. washwashed with methyl tert-butyl ether
  6. concentrationThe filtrate was concentrated in vacuo
  7. filtrationslurrying with hexanes, filtration
  8. customdrying

Sources & evidence

ORD record
ord-4ed766c874474fbebb0808cb7d630a30
Source dataset
uspto-grants-2013_06
Patent number
US08471027B2

Reaction notes

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