Carbamic acid, ethyl ester → 5-(Methoxymethyl)oxazolidin-2-one

HRID 650257Notes

Reaction equation

HRID 650257 reaction equation
[NH2:1]C(OCC)=O.[F-].[K+].[CH3:9][O:10][CH2:11][CH:12]1[CH2:16][O:15][C:14](=O)[O:13]1>CS(C)=O>[CH3:9][O:10][CH2:11][CH:12]1[O:13][C:14](=[O:15])[NH:1][CH2:16]1

Participants

5

Reactant 3

HCID 5641Carbamic acid, ethyl esterHCID 522689Potassium FluorideHCID 43844854-(Methoxymethyl)-1,3-dioxolan-2-one

Product 1

HCID 103131495-(Methoxymethyl)oxazolidin-2-oneYield 68.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

Urethane (82.4 g, 0.925 mol) was dissolved in dimethyl sulfoxide (400 mL), and thereto were added potassium fluoride (48.8 g, 0.841 mol) and 4-methoxymethyl-1,3-dioxolan-2-one (111 g, 0.841 mol), in order. The mixture was stirred for 77 hours at 140° C. under an atmosphere of argon. After filtering off the insoluble materials, the filtrate was condensed in vacuo, and the residue was purified by distillation to give the subject 5-methoxymethyloxazolidin-2-one (76.0 g, yield 68.9%).

Workup

  1. filtrationAfter filtering off the insoluble materials
  2. customcondensed in vacuo
  3. distillationthe residue was purified by distillation

Sources & evidence

ORD record
ord-d575ddc9192b4336a44d6ace852813bc
Source dataset
uspto-grants-2001_08
Patent number
US06271388B1

Reaction notes

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