Diethanolamine → 2-Oxazolidinone, 3-(2-hydroxyethyl)-

HRID 2384506Notes

Reaction equation

HRID 2384506 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][OH:7].[CH3:8][O:9]C(=O)OC.[O-]CC.[Na+]>C(O)C>[OH:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][O:7][C:8]1=[O:9]

Participants

5

Reactant 3

HCID 8113DiethanolamineHCID 12021Dimethyl CarbonateHCID 2723922Sodium ethoxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of equimolar amount of 2-(2-hydroxy-ethylamino)-ethanol and dimethylcarbonate in ethanol (10 mL/g) was added 0.1 eqv. of sodium ethoxide. The mixture thus obtained was refluxed for 3 h and cooled. The mixture was concentrated, then dissolved in dichloromethane. It was then passed through a short pad of silica gel, washed with ethylacetate successively and concentrated to obtain 3-(2-hydroxy-ethyl)-oxazolidin-2-one as colorless oil. The product was used without further purification.

Workup

  1. customThe mixture thus obtained
  2. temperaturewas refluxed for 3 h
  3. temperaturecooled
  4. concentrationThe mixture was concentrated
  5. dissolutiondissolved in dichloromethane
  6. washwashed with ethylacetate successively
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cef136335bcd44fba94a910aacca216f
Source dataset
uspto-grants-2012_09
Patent number
US08263764B2

Reaction notes

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