Ethanolamine → benzyl N-(2-hydroxyethyl)carbamate

HRID 1448482Notes

Reaction equation

HRID 1448482 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].C(=O)([O-])[O-].[Na+].[Na+].[CH2:11]([O:18][C:19](Cl)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CC(C)=O.O>[CH2:11]([O:18][C:19]([NH:1][CH2:2][CH2:3][OH:4])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformate

Product 1

HCID 280458benzyl N-(2-hydroxyethyl)carbamate

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

2-Aminoethanol (20 g.) and sodium carbonate (84.8 g.) is dissolved in acetone-water (1:1) (500 ml.) and benzylchloroformate (83.9 g.) is added dropwise to the stirred solution at 0° C. over a period of 0.5 hours. The mixture is stirred at 0° C. for a further 2.5 hours. The solids are filtered off and washed with acetone and the filtrate is evaporated to dryness. The resulting gum is taken up in chloroform and filtered. The filtrate is evaporated to dryness. The residue is chromatographed on a silica gel column (140×5 cm.) using chloroform and then 10% methanol in chloroform as the eluant to give 2-benzyloxycarbonylaminoethanol, which crystallizes from hexane as colorless needles; m.p. 53°-55° C.; γ max (CCl4) 3450, 3325, 1720, 1510, 1245 cm-1 ; δ (CDCl3) 3.29 (2H, m HOCH2CH2NH--), 3.57 (2H, m, HOCH2CH2NH--), 5.07 (2H, s, --CH2C6H5) and 7.31 ppm (5H, s, --CH2C6H5).

Workup

  1. filtrationThe solids are filtered off
  2. washwashed with acetone
  3. customthe filtrate is evaporated to dryness
  4. filtrationfiltered
  5. customThe filtrate is evaporated to dryness
  6. customThe residue is chromatographed on a silica gel column (140×5 cm.)

Sources & evidence

ORD record
ord-ab6d4a8e56d545e2af48a40dca8652ae
Source dataset
uspto-grants-1979_12
Patent number
US04180565

Reaction notes

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