Реакция #44556

Уравнение реакции

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

2,6-dichloropyrazine

→

title compound

Выход 68.2%

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

Выход 68.2%

Условия реакции

Обработка

1. 1
   ДругоеThe 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
   Фильтрацияfiltered
4. 4
   Другоеthis filtrate crystallised upon storage at low temperature

Методика

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].

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