Trichloroacetonitrile → Tert-butyl 2,2,2-trichloroethanimidate

Potassium t-butoxide (1M in t-butanol), 69 mL (0.069 mole), was dissolved in diethyl ether, 69 mL. This solution was added dropwise, over 30 minutes, to a cold, 0° C., solution of trichloroacetonitrile, 100 g (0.69 mole), in diethyl ether, 69 mL. The mixture was allowed to warm to room temperature over one hour, and was then stirred for an additional hour with heating at reflux. The mixture was cooled to room temperature and evaporated under reduced pressure to yield an oil. The oil was dissolved in hexanes, 140 mL, and filtered to remove potassium salts. The filtrate was evaporated under reduced pressure and the residue was vacuum distilled. The fraction distilling at 2.4 mm Hg and 40° C. was collected. The yield was 105 g, 69% based on trichloroacetonitrile. 1H nmr (300 MHz CDCl3) δ (ppm): 1.58, (s, 9H), 8.21 (br, s, 1H), 13C (75.45 MHz, CDCl3) δ (ppm): 27.23, 83.86, 92.78, 160.33. (Armstrong et al.)

1. additionThis solution was added dropwise, over 30 minutes
2. temperaturewith heating
3. temperatureat reflux
4. temperatureThe mixture was cooled to room temperature
5. customevaporated under reduced pressure
6. customto yield an oil
7. filtration140 mL, and filtered
8. customto remove potassium salts
9. customThe filtrate was evaporated under reduced pressure
10. distillationdistilled
11. distillationThe fraction distilling at 2.4 mm Hg and 40° C.
12. customwas collected

ORD record

ord-b263e2297d154beb954e1a9bb625e781

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703937B2