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

Temperature

130 °C

A mixture of benzamide (0.80 g, 6.60 mmol) and 1,3-dichloropropan-2-one (1.01 g, 7.92 mmol) was heated to 130° C. for 1 hour under nitrogen atmosphere. The crude was purified by crystallization from acetonitrile (25 ml): the suspension was heated to reflux and a brown solution with a white insoluble solid was obtained. It was filtered and the solution was cooled to room temperature. A precipitate formed and the suspension was filtered on a buckner funnel washing with acetonitrile (8 ml). The solid was recovered from the filter, dissolved in EtOAc (20 ml) and washed with 1N NaHCO3 (15 ml). The organic phase was dried (Na2SO4) and evaporated to give 4-(chloromethyl)-2-phenyloxazole (315 mg, 25% yield) as a pale brown solid.

1. customThe crude was purified by crystallization from acetonitrile (25 ml)
2. temperaturethe suspension was heated
3. temperatureto reflux
4. customa brown solution with a white insoluble solid was obtained
5. filtrationIt was filtered
6. temperaturethe solution was cooled to room temperature
7. customA precipitate formed
8. filtrationthe suspension was filtered on a buckner funnel
9. washwashing with acetonitrile (8 ml)
10. customThe solid was recovered from the filter
11. dissolutiondissolved in EtOAc (20 ml)
12. washwashed with 1N NaHCO3 (15 ml)
13. dry with materialThe organic phase was dried (Na2SO4)
14. customevaporated

ORD record

ord-992a7a090fe04bf0bc9a3cf3d87f59c2

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748613B2