Triethylamine → 3-(4-Bromophenyl)-N-methoxy-N-methylprop-2-enamide

4-Bromocinnamic acid (28.3 g, 124.6 mmol), N,O-dimethylhydroxylamine hydrochloride (14.6 g, 149.6 mmol), HOBT (33.7 g, 249.3 mmol), EDAC (47.8 g, 249.3 mmol) and triethylamine (34.7 mL, 249.3 mmol) were added to dichloromethane (800.0 mL). The reaction mixture was stirred at room temperature for 16 hours, quenched with a saturated solution of ammonium chloride, and then extracted with dichloromethane three times. The combined extract was washed with brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2) to give 26.8 g of the titled compound as a white solid.

1. customquenched with a saturated solution of ammonium chloride
2. extractionextracted with dichloromethane three times
3. extractionThe combined extract
4. washwas washed with brine
5. dry with materialdried on anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customto give a yellow liquid residue
8. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2)

ORD record

ord-579933cd42d942d9b70f440e031162a9

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376420B2