Diethyl Carbonate → 2-Oxazolidinone, 3-(2-hydroxyethyl)-

HRID 988695Notes

Reaction equation

HRID 988695 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].[C:8](=O)(OCC)[O:9]CC.C[O-].[Na+]>>[OH:4][CH2:3][CH2:2][N:1]1[CH2:5][CH2:6][O:7][C:8]1=[O:9]

Participants

4

Reactant 3

HCID 7766Diethyl CarbonateHCID 8113DiethanolamineHCID 10942334Sodium Methoxide

Product 1

HCID 768872-Oxazolidinone, 3-(2-hydroxyethyl)-

Conditions

Temperature
135 °C

Procedure

A mixture of diethanolamine (12.55 g), diethyl carbonate (16.2 mL), and sodium methoxide (80 mg) was heated to 130-140° C. for 1.5 h and distilled during the reaction using a Dean-Stark trap. The remaining liquid was concentrated in vacuo to give 15.11 g (97%) as a yellow oil.

Workup

  1. distillationdistilled during the reaction
  2. concentrationThe remaining liquid was concentrated in vacuo
  3. customto give 15.11 g (97%) as a yellow oil

Sources & evidence

ORD record
ord-fcf0eac25975490b95f8dda3d1925ac3
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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