反応 #44556

反応方程式

N-(4-hydroxynaphthalen-1-yl)acetamide

2,6-dichloropyrazine

→

title compound

収率 68.2%

N-(4-(6-Chloropyrazin-2-yloxy)naphthalen-1-yl)acetamide

収率 68.2%

反応条件

後処理

1. 1
   その他The DMF was evaporated in vacuo
2. 2
   workup.DISSOLUTIONThe resulting crude was dissolved in a mixture (hot) of AcOEt (25 mL) and acetone (175 mL)
3. 3
   ろ過filtered
4. 4
   その他this filtrate crystallised upon storage at low temperature

実験手順

Method DD was followed (in a round-bottomed flask, reaction time: 20 hours) with N-(4-hydroxynaphthalen-1-yl)acetamide (1.22 g, 6.08 mmol) and 2,6-dichloropyrazine (1.09 g, 7.30 mmol). The DMF was evaporated in vacuo. The resulting crude was dissolved in a mixture (hot) of AcOEt (25 mL) and acetone (175 mL) and filtered. The volume of the filtrate was reduced to 100 mL and this filtrate crystallised upon storage at low temperature to yield the title compound (1.30 g). Yield: 68%. 1H NMR (500 MHz, DMSO-d6) δ 2.21 (s, 3H), 7.42 (d, 1H, J=8.2 Hz), 7.57 (t, 1H, J=7.5 Hz), 7.64 (t, 1H, J=7.6 Hz), 7.72 (d, 1H, J=8.1 Hz), 7.90 (d, 1H, J=8.3 Hz), 8.16 (d, 1H, J=8.5 Hz), 8.52 (s, 1H), 8.72 (s, 1H), 10.02 (s, 1H). 13C NMR (125.8 MHz, DMSO-d6) δ 23.42, 117.59, 121.40, 121.65, 123.42, 126.53, 126.71, 126.85, 128.90, 131.85, 133.59, 137.50, 144.40, 145.04, 158.92, 169.04. m/z 314.0 [(M+H)+ calcd for C16H12ClN3O2 313.1].

出典