Sodium hydride → HCID 18933661, compound

Participants

Reaction Steps

A solution of N-benzyl-N-methylethanolamine (13.4 g) in dry DMF (30 ml) was added dropwise with stirring to a suspension of sodium hydride (4.75 g, 60% dispersion in mineral oil) in DMF (60 ml) at ambient temperature under nitrogen over 20 minutes. The mixture was stirred and heated at 50° C. for 1 hour until the evolution of hydrogen ceased. The mixture was cooled at ambient temperature and a solution of 2-chloro-6-fluorobenzaldehyde (15.8 g) in DMF (15 ml) was added over 30 minutes. The mixture was heated at 70° C. for 2 hours and then cooled and poured onto ice/water (1 l). The mixture was extracted with ethyl acetate. The combined ethyl acetate extracts were washed with 2M sodium hydroxide solution and then brine, dried and evaporated to give 2-[2-(N-benzyl-N-methylamino)ethoxy]-6-chlorobenzaldehyde as an oil.

Provenance & Evidence