Ethylene Oxide → Hydroxyethyl carbamate

HRID 615697Notes

Reaction equation

HRID 615697 reaction equation
[CH2:1]1[O:3][CH2:2]1.[C:4](=[O:10])([O:6][CH2:7][CH2:8][OH:9])[NH2:5].C(=O)([O-])[O-].[K+].[K+]>>[C:4](=[O:10])([O:6][CH2:7][CH2:8][OH:9])[NH2:5].[OH:3][CH2:2][CH2:1][N:5]1[CH2:8][CH2:7][O:6][C:4]1=[O:10].[O:6]1[CH2:7][CH2:8][NH:5][C:4]1=[O:10]

Participants

6

Reactant 3

HCID 6354Ethylene OxideHCID 11430Potassium CarbonateHCID 21492Hydroxyethyl carbamate

Product 3

HCID 21492Hydroxyethyl carbamateHCID 739492-OxazolidinoneHCID 768872-Oxazolidinone, 3-(2-hydroxyethyl)-

Procedure

In a pressure reactor 26 g of ethylene oxide (0.59 mole) and 60 g of 2-hydroxyethyl carbamate (0.57 mole) are contacted in the presence of 1 g of potassium carbonate (0.0072 mole) at 110° C. for two hours. This resulted in an 85.3 percent conversion of 2-hydroxyethyl carbamate to products, with a selectivity to N-hydroxyethyl-2-oxazolidinone of 9.7 percent and to 2-oxazolidinone of 84.4 percent.

Sources & evidence

ORD record
ord-39c0da7d6811458fb91a1b04df66b0a7
Source dataset
uspto-grants-1985_02
Patent number
US04500717

Reaction notes

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