Methanol → 4-(2-Hydroxyethyl)-2,3-morpholinedione

HRID 1071889Notes

Reaction equation

HRID 1071889 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.CO.[NH:13](CCO)[CH2:14][CH2:15][OH:16]>C(O)(C)C>[OH:16][CH2:15][CH2:14][N:13]1[CH2:10][CH2:9][O:8][C:1](=[O:7])[C:2]1=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 7268Diethyl OxalateHCID 8113Diethanolamine

Product 1

HCID 4584884-(2-Hydroxyethyl)-2,3-morpholinedione

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
2.5 °C

Procedure

A 4(2-hydroxyethyl)morpholine-2,3-dione was prepared at low temperatures by the following procedure. Into a five-necked 22 liter round bottomed flask equipped with a reflux condenser, nitrogen bubbler, addition funnel, thermocouple well, and mechanical stirrer was charged 3000 g (20.53 mol) of diethyl oxalate and 2000 ml of isopropyl alcohol. The solution was cooled to 0 to 5° C. using a cold bath of ice and methanol. A solution of 2160 g (20.53 mol) of diethanolamine dissolved in 2000 ml of isopropyl alcohol was added through the addition funnel during a period of 5 to 6 hours. The reaction is exothermic. After addition was complete, the mixture was allowed to stand at room temperature overnight. The product is collected by filtration. After air drying, 2923 g (89.5% yield) of white crystals were obtained with identical spectral properties to the compound prepared in Example 1.

Workup

  1. customInto a five-necked 22 liter round bottomed flask equipped with a reflux condenser
  2. additionnitrogen bubbler, addition funnel
  3. additionwas added through the addition funnel during a period of 5 to 6 hours
  4. additionAfter addition
  5. filtrationThe product is collected by filtration
  6. customAfter air drying

Sources & evidence

ORD record
ord-1a88f70d0026447cbe7929b604e1e0c2
Source dataset
uspto-grants-2005_06
Patent number
US06908539B2

Reaction notes

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