Sulfuric Acid → 1,7-Diacetamido-3,5-dimethyladamantane

Participants

Reaction Conditions

Reaction Steps

1-Acetamido-3,5-dimethyladamantane (2) (10 g) was added slowly to concentrated sulfuric acid (120 mL) cooled to 0° C. in a salt-ice bath. The solution was stirred at 0° C. for 1 h. Acetonitrile (23 mL) was then added dropwise. The reaction mixture was stirred at 0° C. for 2 h, and then at room temperature for 1 h. The reaction mixture was poured into ice-water. Saturated sodium hydroxide solution was added with cooling. The precipitate (dark solid) was filtered, and discarded. The off-white solid was collected by filtration. Recrystallization afforded 3 as a white solid (6.3 g).

Provenance & Evidence