Dimethylformamide → Stearyl anthranilate

Participants

Reaction Conditions

Reaction Steps

Into a 4 liter beaker equipped with magnetic stirrer, dropping funnel, and thermometer, was charged stearyl alcohol (270.0 grams, 1.0 mol; obtained from Sigma-Aldrich), isatoic anhydride (244.0 grams, 1.5 mol), 1,4-diazabicyclo[2.2.2]octane (DABCO) (56 grams, 0.5 mol), and dimethylformamide (750 milliliters). The mixture was stirred and heated to 120° C. for a period of about 2 hours. The mixture was then cooled to 50° C., and methanol (3 liters) was added. A thick white precipitate formed, which was filtered and then washed with 3×1 liter portions of methanol and oven dried at 60° C. to yield 295.8 grams of a beige solid at 76 percent yield.

Provenance & Evidence