N,N'-Dimethylurea → 4,5-Dihydroxy-1,3-dimethylimidazolidin-2-one

Reaction equation

[C:1]([NH:5][CH3:6])([NH:3][CH3:4])=[O:2].[CH:7]([CH:9]=[O:10])=[O:8].[OH-].[Na+]>>[OH:8][CH:7]1[CH:9]([OH:10])[N:5]([CH3:6])[C:1](=[O:2])[N:3]1[CH3:4]

Participants

Reactant 3

HCID 7293N,N'-Dimethylurea

HCID 7860Glyoxal

HCID 14798Sodium Hydroxide

Product 1

HCID 735394,5-Dihydroxy-1,3-dimethylimidazolidin-2-one

Procedure

Dimethylurea (2 moles, 176 parts) and glyoxal (2 moles, 290 parts of 40% aqueous solution) are mixed and the pH adjusted to 7 with sodium hydroxide. The reaction mixture is stirred at room temperature for several hours and the resulting white solid is filtered, washed with methanol and dried. White crystals, m.p. 140° C., are obtained in fine yield.