N-Ethylaniline → 2-(N-ethylanilino)ethanol

HRID 983572Notes

Reaction equation

HRID 983572 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].Br[CH2:11][CH2:12][OH:13].C([O-])([O-])=O.[K+].[K+]>C(O)CCC>[CH2:1]([N:3]([CH2:11][CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7670N-EthylanilineHCID 108982-BromoethanolHCID 11430Potassium Carbonate

Product 1

HCID 623382-(N-ethylanilino)ethanol

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 101 ml (800 mmol) of freshly distilled N-ethylaniline 14, 71.0 ml (1.00 mol) of 2-bromoethanol, 138 g (1.00 mol) of anhydrous K2CO3 and 8.30 g (50.0 mmol) of anhydrous KI is dissolved in 300 ml of dry n-butanol is refluxed for four days under argon atmosphere and vigorously stirring. After cooling down, the inorganic salts are filtered off and washed with diethylether. The solvents are evaporated under reduced pressure and the crude reaction product is purified by means of a vacuum destillation.

Workup

  1. temperatureis refluxed for four days under argon atmosphere
  2. temperatureAfter cooling down
  3. filtrationthe inorganic salts are filtered off
  4. washwashed with diethylether
  5. customThe solvents are evaporated under reduced pressure
  6. customthe crude reaction product
  7. customis purified by means of a vacuum destillation

Sources & evidence

ORD record
ord-ddea9fabd23e45b0875878e353279176
Source dataset
uspto-grants-2005_03
Patent number
US06864347B2

Reaction notes

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