Ethanolamine → HCID 18753439, compound

HRID 1838606Notes

Reaction equation

HRID 1838606 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)3,5dioxomorpholine (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
  5. temperatureto cool
  6. customwas purified by column chromatography
  7. washeluting with methylene chloride/methanol (9/1)

Sources & evidence

ORD record
ord-cd0851737d2a4f7db5a98b7ab7f5c081
Source dataset
uspto-grants-2004_01
Patent number
US06673803B2

Reaction notes

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