Dichloromethane → N-(4-[1,3]dioxolan-2-yl-2,5-dimethylphenyl)acrylamide

To a 500 mL round-bottom flask was added crude 4-[1,3]dioxolan-2-yl-2,5-dimethylphenylamine (5.6 g, 29 mmol), dichloromethane (100 mL) and diisopropylethylamine (7.6 mL, 43.5 mmol). The resulting mixture was stirred at room temperature until the ingredients dissolved and then the mixture was cooled to 0° C. Acryloyl chloride (2.35 mL, 29 mmol) was then added dropwise over a 5 minute period. The reaction mixture was stirred at 0° C. to 5° C. for 1 hour and then water (50 mL) was added and stirring was continued for about 30 minutes at which time fine solids had formed. The mixture was filtered to collect the solids. The layers of the filtrate were then separated and the organic layer was concentrated under reduced pressure to dryness. Dichloromethane (50 mL) was added to the residue and this mixture was stirred until a free-flowing slurry developed. The slurry was filtered (using the same funnel used to collect the fine solids above) and the filter cake was washed with dichloromethane (10 mL) and dried to provide N-(4-[1,3]dioxolan-2-yl-2,5-dimethylphenyl)acrylamide (3.1 g, 97% purity) as a white to off-white solid.

1. dissolutiondissolved
2. temperaturethe mixture was cooled to 0° C
3. stirringThe reaction mixture was stirred at 0° C. to 5° C. for 1 hour
4. stirringstirring
5. customfine solids had formed
6. filtrationThe mixture was filtered
7. customto collect the solids
8. customThe layers of the filtrate were then separated
9. concentrationthe organic layer was concentrated under reduced pressure to dryness
10. additionDichloromethane (50 mL) was added to the residue
11. stirringthis mixture was stirred until a free-flowing slurry
12. filtrationThe slurry was filtered (
13. customto collect the fine solids above) and the filter cake
14. washwas washed with dichloromethane (10 mL)
15. customdried

ORD record

ord-3974d741ae1943d4a86d158ac485bbf0

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07880010B2