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(E)-N-(4-(2-(3-(Dicyanomethylene)−5,5-dimethylcyclohex-1-en-1-yl)vinyl)phenyl)acetamide (S9)

DJ Da-Yun Jin
XC Xuejie Chen
YL Yizhou Liu
CW Craig M. Williams
LP Lars C. Pedersen
DS Darrel W. Stafford
JT Jian-Ke Tie
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Following Liu et al.74 To a solution of S7 (186 mg, 1 mmol) and 4-acetamidobenzaldehyde (163 mg, 1 mmol) in anhydrous acetonitrile (4 mL) was added piperidine (40 µL, 0.05 mmol) under an argon atmosphere. The mixture was stirred at reflux for 2 h. On cooling to room temperature, the orange precipitation was collected and washed with ice-cooled acetonitrile (3 × 10 mL) to obtain the title compound as an orange solid (254 mg, 77% yield). m.p. > 260 °C. 1H NMR (300 MHz, DMSO-d6) δ 10.12 (s, 1H), 7.67–7.59 (m, 4H), 7.36–7.16 (m, 2H), 6.83 (s, 1H), 2.60 (s, 2H), 2.53 (s, 2H), 2.06 (s, 3H), 1.01 (s, 7H) ppm. 13C NMR (75 MHz, DMSO-d6) δ 170.3, 168.5, 156.2, 140.7, 137.5, 130.6, 128.7, 127.9, 122.1, 118.9, 114.0, 113.2, 75.6, 42.3, 38.2, 31.7, 27.4, 24.1 ppm. LRMS (ESI): m/z (M + H)+: 332.

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