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

To a solution of N-methylformanilide (100 g), butyl vinyl ether (74.12 g) in 85 ml of clorobenzene under stirring at 5° C., a solution of bis-trichloromethylcarbonate (87.84 g) in 170 ml of clorobenzene is added dropwise in 2 hours. The reaction mixture is kept under stirring at room temperature overnight. The mixture is cooled at about 5° C. and the pH is corrected to about 7 by adding sodium hydroxide 15% aqueous solution (348 ml). After separation of the phases, the aqueous layer is extracted with chlorobenzene (90 ml) and the combined organic layers are washed with water (100 ml) and evaporated under reduced pressure. The obtained residue (116.9 g, containing, according to HPLC assay, 104.8 g of pure product, 88% molar yield) is used for the next step of the synthesis without any further purification.

1. temperatureThe mixture is cooled at about 5° C.
2. customAfter separation of the phases
3. extractionthe aqueous layer is extracted with chlorobenzene (90 ml)
4. washthe combined organic layers are washed with water (100 ml)
5. customevaporated under reduced pressure
6. additionThe obtained residue (116.9 g, containing, according to HPLC assay, 104.8 g of pure product, 88% molar yield)
7. customis used for the next step of the synthesis without any further purification

ORD record

ord-38c716d7c7e943708a6e3647fcb2217f

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07091382B2