Ethylene carbonate → Hydroxyethyl carbamate

HRID 615698Notes

Reaction equation

HRID 615698 reaction equation
[C:1](=[O:7])([O:3][CH2:4][CH2:5][OH:6])[NH2:2].C1(=O)O[CH2:11][CH2:10][O:9]1.C(=O)([O-])[O-].[K+].[K+]>>[C:1](=[O:7])([O:3][CH2:4][CH2:5][OH:6])[NH2:2].[O:3]1[CH2:4][CH2:5][NH:2][C:1]1=[O:7].[OH:9][CH2:10][CH2:11][N:2]1[CH2:5][CH2:4][O:3][C:1]1=[O:7]

Participants

6

Reactant 3

HCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 21492Hydroxyethyl carbamate

Product 3

HCID 21492Hydroxyethyl carbamateYield 91%HCID 739492-OxazolidinoneHCID 768872-Oxazolidinone, 3-(2-hydroxyethyl)-

Procedure

In a reactor 30 g of 2-hydroxyethyl carbamate (0.29 mole) are contacted with 25 g of ethylene carbonate (0.29 mole) in the presence of 0.6 g of potassium carbonate (0.0043 mole) at 150° C. for five hours. The reaction results in a conversion of 91 percent of the 2-hydroxyethyl carbamate with a selectivity to 2-oxazolidinone of 53 percent and N-(2-hydroxyethyl)-2-oxazolidinone of 18 percent.

Sources & evidence

ORD record
ord-7c1542a1769940e0ad24b9a6df60329c
Source dataset
uspto-grants-1985_02
Patent number
US04500717

Reaction notes

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