Acetonitrile → 2-(Chloromethyl)-5-(trifluoromethyl)-1,3,4-oxadiazole

Temperature

0 °C

N′-(2-chloroacetyl)-trifluoroacetohydrazide (60 g) and acetonitrile (120 mL) are charged into a round-bottom flask and cooled to about 0° C. Phosphorus oxychloride (27.1 g) is added to the solution for about 15 minutes. The reaction mixture is heated to about 80° C. and stirred for about 28 hours. In a separate vessel, isopropyl acetate (180 mL) and water (180 mL) are mixed and cooled to 0° C. The reaction slurry is added to this solution slowly. The organic layer is separated and washed with 5% sodium bicarbonate solution (180 mL) and finally with 20% sodium chloride solution (180 mL). The organic layer is dried over sodium sulfate. The solvent is completely distilled off under vacuum to afford the title compound. (Yield: 82.2%)

1. temperatureThe reaction mixture is heated to about 80° C.
2. temperaturecooled to 0° C
3. additionThe reaction slurry is added to this solution slowly
4. customThe organic layer is separated
5. washwashed with 5% sodium bicarbonate solution (180 mL) and finally with 20% sodium chloride solution (180 mL)
6. dry with materialThe organic layer is dried over sodium sulfate
7. distillationThe solvent is completely distilled off under vacuum

ORD record

ord-431b1a4cd0b9430ab6495ce64f692555

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309724B2