Ethyl chloroformate → ethyl N-ethoxycarbonyl-2-phenylacetimidate

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-phenylacetimidate hydrochloride (1.7 g, 8.5 mmol) was dissolved in DCM (10.6 mL) and cooled to 0° C. TEA (7.1 mL, 51.1 mmol) was added dropwise the mixture was stirred for 1 h. Ethyl chloroformate (1.6 g, 14.8 mmol) was added and the reaction mixture was allowed to warm to RT and stirred for 12 h. The mixture was diluted with EtOAc (100 mL) and the solids were removed by filtration through diatomaceous earth. The filter cake was washed with EtOAc (3×10 mL) and the combined filtrates were concentrated in vacuo to afford ethyl N-ethoxycarbonyl-2-phenylacetimidate (1.9 g, 93%) as a yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 7.27-7.26 (m, 5H), 4.01-4.00 (m, 4H), 3.70 (s, 2H), 1.18-1.08 (m, 6H).

Provenance & Evidence