Diethyl Oxalate → 4-Methyl-morpholine-2,3-dione

HRID 1594923Notes

Reaction equation

HRID 1594923 reaction equation
[C:1]([O:8]CC)(=O)[C:2]([O:4][CH2:5][CH3:6])=[O:3].[CH3:11][NH:12]C(O)C>C1(C)C=CC=CC=1>[CH3:11][N:12]1[CH2:6][CH2:5][O:4][C:2](=[O:3])[C:1]1=[O:8]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 5247031N-Methylaminoethanol

Product 1

HCID 111371884-Methyl-morpholine-2,3-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Following the procedure of G. Drefahl, M. Hartmann and A. Skurk, Chem. Ber. 1966, 99, diethyl oxalate (1.81 mL, 0.0133 mol) and N-methylamino-ethanol (1 g, 0.0133 mol) were dissolved in toluene(50 mL) and heated at reflux for 5 h. The reaction mixture was concentrated to dryness, triturated with ether, and the residue chromatographed (SiO2, 0-5% MeOH in CH2Cl2) to give the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 h
  3. concentrationThe reaction mixture was concentrated to dryness
  4. customtriturated with ether
  5. customthe residue chromatographed (SiO2, 0-5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-8f23e41991074126ba127bd4f1d5c76a
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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