Triethylamine → 4-(2-Propenyl)-1,2,4-oxadiazolidine-3,5-dione

To a 500 mL round-bottom flask were added acetone (300 mL), allyl isocyanate (12.0 g, 0.145 mol), N-hydroxyurethane (6.1 g, 0.058 mol) and triethylamine (11.7 g, 0.116 mol) respectively at room temperature under nitrogen with efficient stirring. The reaction mixture was allowed to stir at room temperature for 6 d. The solvent was removed under reduced pressure. The residue was suspended in 100 mL of 1N HCl, extracted with ethyl acetate (3×150 mL). The organic solution was washed with water, brine, dried over MgSO4 and concentrated to a clear yellow oil. The crude product was dried under high vacuum for 4 h to give the title compound as an oil (13.1 g) which was used in the next step without further purification.

1. customThe solvent was removed under reduced pressure
2. extractionextracted with ethyl acetate (3×150 mL)
3. washThe organic solution was washed with water, brine
4. dry with materialdried over MgSO4
5. concentrationconcentrated to a clear yellow oil
6. dry with materialThe crude product was dried under high vacuum for 4 h

ORD record

ord-1c9694b018d84fe89c2602412811fbc3

Source dataset

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06737383B1