Dimethyl Sulfoxide → 4-[(2-hydroxyethyl)amino]benzonitrile

HRID 2096059Notes

Reaction equation

HRID 2096059 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH2:10][CH2:11][CH2:12][OH:13].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[OH:13][CH2:12][CH2:11][NH:10][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 700EthanolamineHCID 11430Potassium CarbonateHCID 145174-Fluorobenzonitrile

Product 1

HCID 2946154-[(2-hydroxyethyl)amino]benzonitrileYield 72.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-fluorobenzonitrile (6.06 g), 2-aminoethanol (3.71 g), potassium carbonate (8.29 g) and dimethylsulfoxide (50 mL) was stirred at 100° C. overnight. To the reaction solution was added water (200 mL), and extracted with ethyl acetate (200 mL×4). The ethyl acetate layer was washed with saturated brine (100 mL), and dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (eluted with ethyl acetate:hexane=30:70, then 50:50, then 80:20, then ethyl acetate) to give 4-[(2-hydroxyethyl)amino]benzonitrile as yellow solid (5.89 g).

Workup

  1. extractionextracted with ethyl acetate (200 mL×4)
  2. washThe ethyl acetate layer was washed with saturated brine (100 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (
  6. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-941dfad00f7545169f62fd12c578f48a
Source dataset
uspto-grants-2013_05
Patent number
US08449911B2

Reaction notes

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