Ammonia → 4,4,4-Trifluoro-3,3-dimethylbutanamide

Temperature

0 °C

Treat a 0° C. solution of 4,4,4-trifluoro-3,3-dimethylbutanoic acid [See: US2010/0240663] (17 g, 100 mmol) in acetonitrile (200 mL) with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (23 g, 120 mmol) and 1-hydroxybenzotriazole (16.2 g, 120 mmol), stir at 0° C. for 2 h, treat with concentrated ammonia in water (25 wt %, 15 mL), allow to warm to RT and stir overnight. Remove the organics under reduced pressure, dissolve the residue in EtOAc, and wash with saturated. NaHCO3, then brine, dry over MgSO4, and concentrate to dryness. Treat the material with pet ether, collect the solid via filtration and dry to afford the title compound (13 g, 77% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.46 (s, 1H), 6.93 (s, 1H), 2.19 (s, 2H), 1.18 (s, 6H).

1. temperatureto warm to RT
2. stirringstir overnight
3. customRemove the organics under reduced pressure
4. dissolutiondissolve the residue in EtOAc
5. washwash with saturated
6. dry with materialNaHCO3, then brine, dry over MgSO4
7. concentrationconcentrate to dryness
8. additionTreat the material with pet ether
9. customcollect the solid
10. filtrationvia filtration
11. customdry

ORD record

ord-770ce29f5cfc463d8e7b7f00b901d349

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187474B2