Water → HCID 20183519, compound

Participants

Reaction Steps

A suspension of pre-washed sodium hydride (0.87 g, 0.036 mmol) was stirred at 0° in dry dimethylformamide under nitrogen while N-[2,4-diacetyl-5-hydroxyphenyl]formamide (4.0 g, 18 mmol) was added in small portions. After the addition was complete the mixture was allowed to stir at 0° for 30 minutes, then benzyl bromide (3.lg, 18 mmol) was added all at once. The mixture was stirred for 6 hours during which time the temperature was allowed to rise to 10°. The dark brown solution was poured into a large excess of water, the mixture was acidified to approximately pH 4.0, and was stirred overnight. The off-white solid was filtered off, washed well with water and was dried. The solid was crystallised as white needles 4.8 g (90%) mp 246° -7°.

Provenance & Evidence