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

HRID 1978023Notes

Reaction equation

HRID 1978023 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 to room temperature, filtered, 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 desired product.

Workup

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

Sources & evidence

ORD record
ord-71ce4f63de24430a9be3c438d7e22e8e
Source dataset
uspto-grants-2001_05
Patent number
US06235786B1

Reaction notes

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