Water → 2,2'-Diethyldiphenylamine

HRID 1626244Notes

Reaction equation

HRID 1626244 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. After 20 h additional KOH (10 g) was added, with stirring to reflux continued for an additional 6 h. 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-2bb76ddf101d4767af2a91777009c365
Source dataset
uspto-grants-2014_07
Patent number
US08785434B2

Reaction notes

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