Benzamide → 4-(Chloromethyl)-2-phenyl-1,3-oxazole

Temperature

130 °C

A mixture of benzamide (0.8 g, 6.60 mmol) and 1,3-dichloropropan-2-one (1.00 g, 7.92 mmol) was heated at 130° C. stirring under nitrogen atmosphere for 1 hour (UPLC/MS complete conversion). The obtained brown solution was cooled to room temperature, and the brown solid was suspended in acetonitrile (25 ml) and heated to reflux. The white insoluble solid was eliminated by filtration, and the solution was allowed to cool to room temperature. The formed precipitate was collected by filtration and washed with acetonitrile (8 ml), dissolved in EtOAc (20 ml) and washed with aq. NaHCO3 (15 ml). The organic phase was dried (Na2SO4), filtered and evaporated to obtain 4-(chloromethyl)-2-phenyloxazole (315 mg, 24.7% yield).

1. temperatureThe obtained brown solution was cooled to room temperature
2. temperatureheated to reflux
3. filtrationThe white insoluble solid was eliminated by filtration
4. temperatureto cool to room temperature
5. filtrationThe formed precipitate was collected by filtration
6. washwashed with acetonitrile (8 ml)
7. dissolutiondissolved in EtOAc (20 ml)
8. washwashed with aq. NaHCO3 (15 ml)
9. dry with materialThe organic phase was dried (Na2SO4)
10. filtrationfiltered
11. customevaporated

ORD record

ord-76ab54328e1b470295fb669bf3529884

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563577B2