Potassium Carbonate → 3-(3,4,4-Trimethyl-2,5-dioxoimidazolidin-1-yl)-2-methoxymethyloxy-prop-1-ene

HRID 1597412Notes

Reaction equation

HRID 1597412 reaction equation
[CH3:1][N:2]1[C:8]([CH3:10])([CH3:9])[C:6](=[O:7])[NH:5][C:3]1=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH3:17][O:18][CH2:19][O:20][C:21](=[CH2:24])[CH2:22]Cl>CN(C=O)C>[CH3:1][N:2]1[C:8]([CH3:10])([CH3:9])[C:6](=[O:7])[N:5]([CH2:24][C:21]([O:20][CH2:19][O:18][CH3:17])=[CH2:22])[C:3]1=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 812951,5,5-Trimethylimidazolidine-2,4-dioneHCID 106782943-Chloro-2-(methoxymethoxy)prop-1-ene

Product 1

HCID 217002333-(3,4,4-Trimethyl-2,5-dioxoimidazolidin-1-yl)-2-methoxymethyloxy-prop-1-eneYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1,5,5 trimethylhydantoin (7.0 g, 49.2 mmol), powdered potassium carbonate (8.16 g, 59 mmol) and 2-methoxymethyloxy-allyl chloride (7.65 g, 56 mmol) in dry DMF (100 mL) was heated to 100° C. with stirring for 1.5 h. The reaction mixture was cooled, fliltered and the filtrate was concentrated, then partitioned between ethyl acetate and water. The organic extract was washed twice with water, brine, dried and concentrated, then purified via silica gel chromatography eluting with 50% ethyl acetate: hexane to give 10.58 g (89%) of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationthe filtrate was concentrated
  3. custompartitioned between ethyl acetate and water
  4. extractionThe organic extract
  5. washwas washed twice with water, brine
  6. customdried
  7. concentrationconcentrated
  8. custompurified via silica gel chromatography
  9. washeluting with 50% ethyl acetate

Sources & evidence

ORD record
ord-6a44f87154ca4a7f97e09c94a115e08e
Source dataset
uspto-grants-2001_09
Patent number
US06294573B1

Reaction notes

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