Ethanolamine → 2-Benzamidoethanol

HRID 1764865Notes

Reaction equation

HRID 1764865 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1COCC1>[OH:2][CH2:1][CH2:3][NH:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 7412Benzoyl chloride

Product 1

HCID 5695262-BenzamidoethanolYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethanolamine (1.09 g, 17.8 mmol) in THF was added benzoyl chloride (520 mg, 3.60 mmol) dropwise at 0° C. under N2 atmosphere. The reaction mixture was stirred for 10 min and then quenched with 1M HCl. The mixture was then diluted with EtOAc and washed with sat. aq. NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was crystallized to give N-(2-hydroxyethyl)benzamide (593 mg, 97%) as a white crystalline solid. 1H NMR (CDCl3, 300 MHz) δ3.41 (s, 1H), 3.49-3.59 (m, 2H), 3.75 (t, 2H, J=5.2 Hz), 7.10 (s, 1H), 7.32-7.38 (m, 2H), 7.42-7.48 (m, 1H), 7.72-7.76 (m, 2H) ppm.

Workup

  1. customquenched with 1M HCl
  2. additionThe mixture was then diluted with EtOAc
  3. washwashed with sat. aq. NaHCO3 and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized

Sources & evidence

ORD record
ord-681b9d022f834fd8b9cc5e3c67e601f2
Source dataset
uspto-grants-2007_06
Patent number
USRE039679E1

Reaction notes

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