Ethylene Oxide → 1-(2-Hydroxyethyl)-5,5-dimethylimidazolidine-2,4-dione

HRID 2372803Notes

Reaction equation

HRID 2372803 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[CH2:10]1[O:12][CH2:11]1.[OH-].[Na+]>>[OH:12][CH2:11][CH2:10][N:6]1[C:2]([CH3:9])([CH3:1])[C:3](=[O:8])[NH:4][C:5]1=[O:7]

Participants

4

Reactant 3

HCID 6354Ethylene OxideHCID 6491DimethylhydantoinHCID 14798Sodium Hydroxide

Product 1

HCID 156467931-(2-Hydroxyethyl)-5,5-dimethylimidazolidine-2,4-dione

Procedure

Thus, to make the non-methylolated hydantoin fatty acid ester, or MHEDMH ester (Ia), 5,5-dimethylhydantoin, or DMH (ii) [C5H8O2N2 =128 mol. wt.], is reacted with ethylene oxide in a first step per reaction scheme (1a), e.g. in the presence of a catalyst such as sodium hydroxide, to form monohydroxyethyl dimethylhydantoin, or 1-(2-hydroxyethyl)-5,5-dimethylhydantoin [i.e., 1-(2-hydroxyethyl)-5,5-dimethyl-1,3-diazacyclopentane-2,4-dione], or MHEDMH (vi) [C7H12O3N2 =172 mol. wt⟧

Sources & evidence

ORD record
ord-8f9a4b48c80f4b4fb5ec5aaa5e88d9ea
Source dataset
uspto-grants-1992_03
Patent number
US05100907

Reaction notes

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