3-Methoxyaniline → 3-Methoxy-N,N-diphenylaniline

HRID 1168655Notes

Reaction equation

HRID 1168655 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.I[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1O[CH2:33][CH2:32]OCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>C1(OC2C=CC=CC=2)C=CC=CC=1.[Cu]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]([C:33]2[CH:32]=[CH:5][CH:4]=[CH:3][CH:8]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 108243-MethoxyanilineHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 2855718-Crown-6

Product 1

HCID 147467193-Methoxy-N,N-diphenylaniline

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7583Diphenyl EtherSolvent

Procedure

3-methoxytriphenylamine was prepared by a phase transfer variant of the Ullmann coupling procedure (S. Gauthier and J. M. J. Fréchet, Synthesis, 1987, 1331) in which 37.34 g m-Anisidine, 142.47 g iodobenzene, 74.93 g copper powder, 2.20 g 18-crown-6 and 320.8 g anhydrous potassium carbonate in 500 ml phenyl ether were placed into a 1 liter three necked round bottom flask equipped with overhead stirrer, reflux condenser, nitrogen inlet, thermowell, and heating mantle and heated at reflux overnight. The solids were removed by filtration and the solvents by vacuum distillation. The resulting brown oil is used in step 2 below.

Workup

  1. customequipped with overhead stirrer
  2. temperaturereflux condenser, nitrogen inlet
  3. temperaturethermowell, and heating mantle
  4. temperatureheated
  5. temperatureat reflux overnight
  6. customThe solids were removed by filtration
  7. distillationthe solvents by vacuum distillation

Sources & evidence

ORD record
ord-e298de9ff27f4050b5cd27390b556704
Source dataset
uspto-grants-2003_09
Patent number
US06627111B2

Reaction notes

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