Ethanolamine → HCID 18753439, compound

HRID 547230Notes

Reaction equation

HRID 547230 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[C:5]1(=O)[O:11][C:9](=[O:10])[CH2:8][O:7][CH2:6]1>N1C=CC=CC=1>[OH:2][CH2:1][CH2:3][N:4]1[C:9](=[O:10])[CH2:8][O:7][CH2:6][C:5]1=[O:11]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 782321,4-Dioxane-2,6-dione

Product 1

HCID 18753439HCID 18753439, compoundYield 12.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethanolamine (2.44 g, 40 mmol) was added dropwise to a solution of diglycolic anhydride (2.32 g, 20 mmol) in pyridine (10 ml). The mixture was stirred for 5 minutes at ambient temperature and then heated at reflux for 2 hours. The volatiles were removed by evaporation and the residue was heated at 180° C. for 2 hours The reaction mixture was allowed to cool and was purified by column chromatography eluting with methylene chloride/methanol (9/1) to give 4-(2-hydroxyethyl)-3,5-dioxomorpholine (400 mg, 12.5%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customThe volatiles were removed by evaporation
  4. temperaturethe residue was heated at 180° C. for 2 hours The reaction mixture
  5. temperatureto cool
  6. customwas purified by column chromatography
  7. washeluting with methylene chloride/methanol (9/1)

Sources & evidence

ORD record
ord-368fddedbf9f40acbc98d82e200c346f
Source dataset
uspto-grants-2011_05
Patent number
USRE042353E1

Reaction notes

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