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 dropwise 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 concentrated in vacuo, 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 EtOAc/hexanes) to obtain 3-(trifluoromethyl)isoxazol-5-amine (1.38 g, 37% yield). MS (ESI) m/z: 153.0 (M+H+).

1. concentrationThe solution was concentrated in vacuo
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 EtOAc/hexanes)

ORD record

ord-c9d261f8f78b4c91b263dc66774f5a14

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143293B2