Ethanolamine → benzyl N-(2-hydroxyethyl)carbamate

HRID 345905Notes

Reaction equation

HRID 345905 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].Cl[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].C(OCC)(=O)C>C(Cl)Cl>[CH2:9]([O:8][C:6]([NH:4][CH2:3][CH2:1][OH:2])=[O:7])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8857Ethyl AcetateHCID 10387Benzyl chloroformate

Product 1

HCID 280458benzyl N-(2-hydroxyethyl)carbamateYield 94.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To ethanolamine (9.0 ml, 149 mmol) in methylene chloride (100 ml) at 0° C. was added benzyl chlorformate (10.0 ml, 70 mmol). The mixture was stirred at 0° C. for 30 min, then at room temperature for 1 h, poured into ethyl acetate, washed with 2M HCl, saturated NaHCO3 solution, and brine, then dried over Na2SO4 and evaporated to provide 12.91 g (94%) of the desired compound as a white solid. 1H NMR (CDCl3, TMS) 7.47 (m,5H), 5.11 s,2H), 3.73 (m,2H), 3.38 (m,2H).

Workup

  1. waitat room temperature for 1 h
  2. washwashed with 2M HCl, saturated NaHCO3 solution, and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-16ebb065b3f54bd6bf06620dc74a6728
Source dataset
uspto-grants-1991_10
Patent number
US05059589

Reaction notes

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