2-(Ethylamino)ethanol → 4-(Ethyl(2-hydroxyethyl)amino)benzaldehyde

HRID 6197

Reaction equation

HRID 6197 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10]([NH:12][CH2:13][CH2:14][OH:15])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[OH:15][CH2:14][CH2:13][N:12]([C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 80722-(Ethylamino)ethanolHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 6398574-(Ethyl(2-hydroxyethyl)amino)benzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

To a three neck flask fitted with a mechanical stirrer, a thermometer, and a condenser, is added 124 g (1 mole) of 4-fluorobenzaldehyde, 89.1 g (1 mole) of 2-(N-ethylamino)ethanol, 138.2 g (1 mole) of anhydrous potassium carbonate, and dimethylsulfoxide. The mixture is heated at 95° C. for 3 hours. After cooling to room temperature, the solution is poured into a four-fold excess of ice water, and the solid product is collected by filtration and recrystallized from water.

Workup

  1. customTo a three neck flask fitted with a mechanical stirrer
  2. temperatureAfter cooling to room temperature
  3. filtrationthe solid product is collected by filtration
  4. customrecrystallized from water

Sources & evidence

ORD record
ord-5e96e77a6ea242f0b4bfc5496ffdd983
Source dataset
uspto-grants-1993_09
Patent number
US05247042

Linked notes

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