Ethanol → Ethyl 2,2-dimethylpropanecarboximidate

Pivalonitrile (13 g, 157 mmol) was dissolved in absolute ethanol (50 mL) and cooled in a salt-ice bath. HCl gas was bubbled through this solution for 1 h to saturate the solution. The reaction was warmed to RT. After 3 hr, the solvent was removed in vacuo to afford ethyl pivalimidate (16 g, 62%) as white solid. The crude ethyl pivalimidate (16 g, 97 mmol) was taken up in absolute ethanol (20 mL) and absolute ethanol saturated with ammonia (30 mL) was added. The reaction mixture was stirred at RT for 3 hr, whereupon ammonium chloride was filtered off and the salt washed with ethanol. The filtrate was concentrated in vacuo and the solid obtained was dried under vacuum to afford compound O.1, pivalimidamide (10 g, 76%). 1H NMR (DMSO-d6, 200 MHz): δ 8.6 (br s, 1H), 1.2 (s, 9H); LCMS m/z 101 [M+1]+.

1. temperaturecooled in a salt-ice bath
2. customHCl gas was bubbled through this solution for 1 h
3. concentrationto saturate the solution
4. customthe solvent was removed in vacuo

ORD record

ord-49491ffb88014550a2d779d0178a2d39

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802657B2