Ethanolamine → benzyl N-(2-hydroxyethyl)carbamate

HRID 1167670Notes

Reaction equation

HRID 1167670 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].Cl[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].C(N(CC)CC)C>ClCCl>[OH:4][CH2:3][CH2:2][NH:1][C:6](=[O:7])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 10387Benzyl chloroformate

Product 1

HCID 280458benzyl N-(2-hydroxyethyl)carbamateYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

944 mg(15.46 mmol) of 2-aminoethanol was dissolved in 50 ml of dichloromethane, and then 1.8 ml(12.88 mmol) of benzyl chloroformate and 2.7 ml(19.32 mmol) of triethylamine were added thereto. The mixture was stirred at room temperature for one hour. After the reaction was completed, the mixture was concentrated and 50 ml of water was added thereto to obtain a white solid. The obtained white solid was filtered and dried to give 1.94 g(9.93 mmol) of the title compound in a yield of 77%.

Workup

  1. concentrationthe mixture was concentrated
  2. addition50 ml of water was added
  3. customto obtain a white solid
  4. filtrationThe obtained white solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-df2e648af176461795d38f96dc340eb3
Source dataset
uspto-grants-2003_09
Patent number
US06620831B2

Reaction notes

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