Butyl vinyl ether → N-Methyl-N-phenylprop-2-enamide

To a solution of N-methylformanilide (30 g), butyl vinyl ether (22.2 g) in 25 ml of clorobenzene under stirring at 10° C., a solution of bis-trichloromethylcarbonate (24.3 g) in 50 ml of clorobenzene is added dropwise in 2 hours. The reaction mixture is kept under stirring at room temperature overnight. Water (50 ml) is added, the mixture is cooled at about 5–10° C. and the pH is corrected to about 7 by adding sodium hydroxide 30% aqueous solution (50 ml). After separation of the phases, the aqueous layer is extracted with chlorobenzene (50 ml) and the combined organic layers are washed with water (20 ml) and evaporated under reduced pressure. To the residue tert-butyl methyl ether (50 ml) is added and the mixture is cooled at −15° C. for 1 hour. The precipitate is filtered on Buchner, washed twice with tert-butyl methyl ether (25 ml×2) and dried at 30–35° C. under vacuum overnight. 24.66 g of pure compound are obtained (69% molar yield)

1. temperaturethe mixture is cooled at about 5–10° C.
2. customAfter separation of the phases
3. extractionthe aqueous layer is extracted with chlorobenzene (50 ml)
4. washthe combined organic layers are washed with water (20 ml)
5. customevaporated under reduced pressure
6. additionTo the residue tert-butyl methyl ether (50 ml) is added
7. temperaturethe mixture is cooled at −15° C. for 1 hour
8. filtrationThe precipitate is filtered on Buchner
9. washwashed twice with tert-butyl methyl ether (25 ml×2)
10. customdried at 30–35° C. under vacuum overnight

ORD record

ord-d2c6fe20e4d64de2bcd48d7fe2059e60

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07091382B2