Ethanolamine → benzyl N-(2-hydroxyethyl)carbamate

HRID 992455Notes

Reaction equation

HRID 992455 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH2:12]([CH2:14][NH2:15])[OH:13]>O1CCCC1>[OH:13][CH2:12][CH2:14][NH:15][C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 10387Benzyl chloroformate

Product 1

HCID 280458benzyl N-(2-hydroxyethyl)carbamateYield 41.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl chloroformate (63 mL, 443 mmol) was added dropwise to a solution of ethanolamine (60 g, 984 mmol) in tetrahydrofuran (300 mL). After being stirred overnight, the mixture was concentrated in vacuo, and partitioned between methylene chloride and dilute aqueous HCl. The separated organic layer was washed with dilute aqueous NaHCO3, dried (MgSO4), filtered, and concentrated in vacuo to give the title compound (36 g) which was used without further purification in the next step.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. custompartitioned between methylene chloride and dilute aqueous HCl
  3. washThe separated organic layer was washed with dilute aqueous NaHCO3
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e0bc07828224236ac5f04990b252d42
Source dataset
uspto-grants-2002_10
Patent number
US06469029B1

Reaction notes

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