Ammonia → 4,4,4-trifluorobutanamide

To a solution of 4,4,4-trifluorobutanoic acid (19.9 g) in THF (200 mL) were added oxalyl chloride (30.5 mL) and DMF (0.54 mL) at 0° C., and the mixture was stirred for 4 hr. The obtained reaction mixture was added to 28% aqueous ammonia (150 mL) at 0° C., and the mixture was stirred for 1 hr. The reaction mixture was filtration, and the filtrate was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained solid was suspended in diisopropyl ether. The precipitate was collected by filtration, washed with diisopropyl ether, and dried to give the title compound (17.9 g) as a solid.

1. customThe obtained reaction mixture
2. stirringthe mixture was stirred for 1 hr
3. filtrationfiltration
4. extractionthe filtrate was extracted with ethyl acetate
5. washThe extract was washed with saturated brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. filtrationThe precipitate was collected by filtration
9. washwashed with diisopropyl ether
10. customdried

ORD record

ord-f1718379c0fe484c8a2c37e10a1e7cbd

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09023858B2