Ethanolamine → 4-{2-[(2-Hydroxyethyl)amino]ethoxy}benzonitrile

HRID 899121Notes

Reaction equation

HRID 899121 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1.[CH2:13]([CH2:15][NH2:16])[OH:14]>>[OH:14][CH2:13][CH2:15][NH:16][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 24522124-(2-Bromoethoxy)benzonitrile

Product 1

HCID 690686254-{2-[(2-Hydroxyethyl)amino]ethoxy}benzonitrile

Conditions

Temperature
120 °C

Procedure

4-(2-Bromoethoxy)benzonitrile (30 g, 0.133 mol; see step (i) above) and ethanolamine (48 mL, 0.78 mol) were mixed and refluxed, under a nitrogen atmosphere, at about 120° C. for 3 h. The reaction was quenched by addition of a sodium hydroxide solution to the mixture. The sub-title compound was extracted using DCM (2×250 mL), which was dried over anhydrous sodium sulfate and then concentrated. Yield: 13.1 g (48%).

Workup

  1. customThe reaction was quenched by addition of a sodium hydroxide solution to the mixture
  2. extractionThe sub-title compound was extracted
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-00d4aad05e8c4e0792eb2acf6c3fe321
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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