反应详情

Adamantan-1-ylcyanamide (299 mg, 1.70 mmol) and o-iodoaniline hydrochloride (433 mg 1.70 mmol) were finely ground together and heated at 200° for 10 min. The resultant black glassy solid was pulverized, and recrystallized 5 times from EtOH/Et2O. The resultant faintly blue needles (80 mg) were dissolved in 4 ml EtOH, and passed through a short (<1 cm) column packed from bottom to top with Celite, charcoal, activated alumina, and sand. The colorless eluate was then diluted with 5 ml Et2O, and allowed to stand in an Et2O diffusion chamber overnight. The white needles were collected by suction filtration, 40 mg, mp 274°-275°C. Addition of another 5 ml Et2O yielded a second crop (31 mg) of identical material. Combined yield: 21%. 1H (CD3OD) 1.779 (s, 6H), 2.090 (s, 6H), 2.164 (s, 3 H), 7.168 (t, 1H, J=8.1 Hz), 7.388 (d, 1 H, J=9.1 Hz), 7.503 (t, 1 H, J=7.8 Hz), 8.004 (d, 1 H, J=7.8 Hz).

1. temperatureheated at 200° for 10 min
2. customrecrystallized 5 times from EtOH/Et2O
3. dissolutionThe resultant faintly blue needles (80 mg) were dissolved in 4 ml EtOH
4. additionThe colorless eluate was then diluted with 5 ml Et2O
5. customto stand in an Et2O diffusion chamber overnight
6. filtrationThe white needles were collected by suction filtration, 40 mg, mp 274°-275°C
7. additionAddition of another 5 ml Et2O