Dimethylformamide → HCID 178421234, compound

Participants

Reaction Conditions

Reaction Steps

4,7,7-Trimethyl-3-oxo-N-[4-(cyanomethyl)phenyl]-2-oxabicyclo[2.2.1]-heptane-1-carboxamide (6 g, prepared in the preceding paragraph), sodium azide (6.24 g), ammonium chloride (5.1 g) and dimethylformamide (100 mL) were heated in a 135° C. oil bath for 20 hours under a nitrogen atmosphere. Water was added to the hot mixture until homogeneity was achieved. The mixture was then cooled to room temperature, poured onto saturated brine solution in a separatory funnel, and extracted with ethyl acetate. The extracts were washed with saturated brine solution, dried over MgSO4 and concentrated in a rotary evaporator. The crude product was dissolved in hot acetone, then cooled in a 0° C. freezer to yield 4.1 g. (60% yield) of the title compound as a dark yellow solid; m.p. 224°-225° C. (dec.).

Provenance & Evidence