Potassium Cyanide → 3-(Trifluoromethyl)-1,2-oxazol-5-amine

To a suspension of KCN (1.90 g, 29.1 mmol) in MeOH (35 mL) was added dropwisely 3-bromo-1,1,1-trifluoropropan-2-one oxime (5.00 g, 24.3 mmol) in MeOH (72 mL) at RT. The reaction mixture was stirred at RT for 3 hours. The solution was evaporated and then the residue was dissolved in EtOAc and stirred at RT. The solid was filtered and the filtrate was evaporated to obtain the crude product. The crude product was purified by silica gel column chromatography (Biotage: 25M, 10% to 60% EtOAc/hexane: 550 mL) to obtain 3-(trifluoromethyl)isoxazol-5-amine (1.38 g, 37% yield). MS (ESI) m/z: 153.0 (M+H+).

1. customThe solution was evaporated
2. dissolutionthe residue was dissolved in EtOAc
3. stirringstirred at RT
4. filtrationThe solid was filtered
5. customthe filtrate was evaporated
6. customto obtain the crude product
7. customThe crude product was purified by silica gel column chromatography (Biotage: 25M, 10% to 60% EtOAc/hexane: 550 mL)

ORD record

ord-de0cc88056ac40a7b803f939e2f85416

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188113B2