Acetic Acid → HCID 14028596, compound

Participants

Reaction Conditions

Reaction Steps

Glacial acetic acid (200 ml) and 2,2'-diiodobenzidine (20.0 g, 49 mmol) were stirred at room temperature for 20 minutes, and then 100 ml 48% tetrafluoroboric acid was added to the solution. After 30 minutes, the acidic solution was cooled to -5° C., and a sodium nitrite solution (7.2 g NaNO2 in 80 ml water) was slowly added to maintain the temperature below 0° C. The reaction was stirred for 1 hour at 0° C., and the precipitate which formed was filtered and dried for 18 hours under vacuum. The dried product was added over a period of 1 hour to a solution of 2 L water containing 30 ml 85% phosphoric acid at 75° C. Nitrogen was evolved, and heating continued until the evolution of gas was complete (approx. 30 min.). The reaction was cooled to room temperature, the orange product filtered, and recrystallized from 3:1 water:ethanol. A white crystalline product, II, mp 171°-172° C., was collected in 25% yield.

Provenance & Evidence