Triethylamine → phenyl 2-[4-(2-ethyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethylcarbamate

Participants

Reaction Steps

To a stirred solution of 2-[4-(2-ethyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethylamine (step 4 of EXAMPLE 3, 1.72 g, 5.9 mmol) and triethylamine (2.0 mL, 14.8 mmol) in dichloromethane (60 mL) was added phenyl chloroformate (900 μL, 7.0 mmol) at ambient temperature. After 1 h, the reaction mixture was partitioned between ethyl acetate (30 mL) and water (10 mL). The aqueous phase was extracted with ethyl acetate (3×30 mL) and the combined organic phase was dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 3:1 to 1:1) to afford 2.0 g (83%) of the title compound as colorless amorphous: MS (ESI) m/z 412 [M+H]+, 1H-NMR (CDCl3)δ1.27 (3H, d, J=7.5 Hz), 2.73 (2H, t, J=7.5 Hz), 2.99 (2H, t, J=7.1 Hz,) 3.59 (2H, t, J=7.0 Hz), 5.12 (1H, br), 7.12 (2H, d, J=7.5 Hz), 7.18-7.25 (2H, m), 7.29-7.41 (8H, m) 7.80 (2H, dd, J=8.3, 1.3 Hz).

Provenance & Evidence