Ethyl isocyanatoacetate → HCID 66816429, compound

Ethyl isocyanatoacetate (581 mg, 4.50 mmol) and N,N-diisopropylethylamine (426 mg, 1.65 mmol) were added to a solution of 4-bromo-2,6-dimethylaniline (600 mg, 3.00 mmol) in toluene (6 ml) with stirring in a nitrogen stream, and the mixture was heated with stirring at 120° C. After 30 minutes, the reaction solution was brought to room temperature, and the precipitate was collected by filtration, washed with toluene and then dried under reduced pressure. The resulting solid was suspended in toluene (6 ml). DBU (68.4 mg, 2.25 mmol) was added and the mixture was heated with stirring at 120° C. After 30 minutes, the reaction solution was brought to room temperature and diluted with ethyl acetate, and the organic layer was washed with a 1 N aqueous hydrochloric acid solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the magnesium sulfate was then removed by filtration. The filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography (hexane-ethyl acetate) to give 3-(4-bromo-2,6-dimethyl-phenyl)-imidazolidine-2,4-dione (570 mg, 67%).

1. temperaturethe mixture was heated
2. stirringwith stirring at 120° C
3. customwas brought to room temperature
4. filtrationthe precipitate was collected by filtration
5. washwashed with toluene
6. customdried under reduced pressure
7. temperaturethe mixture was heated
8. stirringwith stirring at 120° C
9. waitAfter 30 minutes
10. customwas brought to room temperature
11. washthe organic layer was washed with a 1 N aqueous hydrochloric acid solution and saturated brine
12. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
13. customthe magnesium sulfate was then removed by filtration
14. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-91a59b825f124942b0fb49266daad5df

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169254B2