N,N'-Dimethylurea → 1,3-Dimethylimidazolidine-2,4-dione

HRID 2080609Notes

Reaction equation

[CH:1]([CH:3]=O)=[O:2].C(N(CC)CC)C.[CH3:12][NH:13][C:14]([NH:16][CH3:17])=[O:15]>O>[CH3:12][N:13]1[CH2:3][C:1](=[O:2])[N:16]([CH3:17])[C:14]1=[O:15]

Participants

Conditions

Temperature: 30 °C

Procedure

In a 1000 ml glass vessel equipped with a stirrer, thermometer, a dropping funnel and a distillation unit was charged 290 g (2.0 mol) of 40 wt % aqueous glyoxal solution. And then, triethylamine is added thereto to prepare a basic mixed solution (At this time, the solution had a pH of 9). To the mixed solution was gradually added dropwise a solution comprising 176 g (2.0 mol) of 1,3-dimethylurea and 176 ml of water while maintaining a liquid temperature to 25 to 35° C. After stirring the solution at room temperature for 3 hours, the mixture was reacted by elevating the temperature to 200° C. over 2 hours while removing triethylamine and water under normal pressure by distillation. After completion of the reaction, the obtained reaction mixture was distilled under reduced pressure (105 to 107° C./0.67 to 1.33 kPa) to obtain 217 g (Isolation yield; 85%) of 1,3-dimethylimidazolidin-2,4-dione as a pale yellowish liquid.

Workup

customIn a 1000 ml glass vessel equipped with a stirrer
customto prepare a basic mixed solution (At this time
customthe mixture was reacted
customto 200° C.
customover 2 hours
customwhile removing triethylamine and water under normal pressure
distillationby distillation
customAfter completion of the reaction
customthe obtained reaction mixture
distillationwas distilled under reduced pressure (105 to 107° C./0.67 to 1.33 kPa)

Sources & evidence

ORD record: ord-8ba7c2a8b0944e0089f35470fd41284f
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932400B2

Reaction notes

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