Water → 2,2'-Diethyldiphenylamine

HRID 408111Notes

Reaction equation

HRID 408111 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][CH3:20])C(=O)C)[CH3:2].[OH-].[K+].O>CCO>[CH2:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[NH:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:1][CH3:2])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium Hydroxide2×HCID 67383896N,N-bis(2-ethylphenyl)acetamide

Product 1

HCID 1166492,2'-DiethyldiphenylamineYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The N,N-bis(2-ethylphenyl)acetamide (8.1 g, 30.30 mmol) and KOH (5 g), in EtOH (50 mL), was stirred and heated to reflux overnight. 20 hrs later additional KOH (10 g) was added, wth stirring to reflux continued for an additional 6 hrs. It was cooled, poured into H2O (125 mL) and extracted with ethyl acetate (2×350 mL). The combined organics were washed with brine, dried (MgSO4), filtered and concentrated to dryness, affording a dark red oil (5.8 g, 85%).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. temperatureto reflux
  4. temperatureIt was cooled
  5. extractionextracted with ethyl acetate (2×350 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2ae85cf9a69b442ca5e224b77ab2b2d1
Source dataset
uspto-grants-2014_06
Patent number
US08759336B2

Reaction notes

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