反应详情

1,1,1-Tris(4-(4-aminophenoxy)phenyl)ethane (Example 2; 0.580 g, 1.00 mmol), N-(4-nitrosophenyl)acetamide (Example 3; 0.985 g, 6 mmol) and acetic acid (20 mL) were charged into a 150 mL round-bottomed flask equipped with a magnetic stir bar. The mixture was stirred at room temperature for 48 hours. The mixture was at first turned into a greenish solution, and then yellow particles started to precipitate out of the solution. The mixture was diluted by deionized water (100 mL). Solids were collected and washed with water (500 mL), followed by ethanol (200 mL) to remove most of the unreacted nitroso reagent. The solid was then extracted by hot acetone (100 mL) four times. The acetone extract was concentrated on a rotary evaporator to give yellow solids as raw product. The raw product was slurried in hot ethanol (50 mL) and filtered twice after cooling to room temperature in between to give 0.62 g (61%) of yellow solids, mp 220° C. (dec.). 1H-NMR (d6-DMSO, δ in ppm): 2.09 (s, 9H, COCH3), 2.15 (s, 3H, CCH3) 7.03-7.15 (m, 18H), 7.79-7.87 (m, 18H) 10.28 (s, 3H, NHCO). 13C-NMR (d6-DMSO, δ in ppm): 24.16, 30.28, 51.00, 118.50, 118.86, 119.18, 123.42, 124.35, 129.99, 142.09, 144.50, 147.38, 147.77, 153.78, 159.07, 168.06.

1. customequipped with a magnetic stir bar
2. customto precipitate out of the solution
3. additionThe mixture was diluted by deionized water (100 mL)
4. customSolids were collected
5. washwashed with water (500 mL)
6. customto remove most of the unreacted nitroso reagent
7. extractionThe solid was then extracted by hot acetone (100 mL) four times
8. extractionThe acetone extract
9. concentrationwas concentrated on a rotary evaporator
10. customto give yellow solids as raw product
11. filtrationfiltered twice
12. temperatureafter cooling to room temperature in between