Molecules 2015, 20
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1-Benzyl-2-(3-chlorophenyl)-4,5-diphenyl-1H-imidazole (5): Yield: 93%. m.p.: 144–146°C; IR (KBr, cm−1):
2980, 1610, 1521, 1410, 1122, 790. 1H-NMR (400 MHz, CDCl3) δH: 5.12 (s, 2H), 6.82 (s, 2H), 7.19–7.29
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(m, 8H), 7.34–7.41 (m, 8H), 7.61 (t, J = 7.4 Hz, 1H), 7.67 (d, J = 7.4 Hz, 1H). C-NMR (100 MHz,
CDCl3) δC: 48.30, 125.87, 126.02, 126.40, 126.53, 126.81, 127.38, 127.54, 128.11, 128.16, 128.26,
128.59, 128.62, 128.64, 128.73, 128.80, 128.82, 128.85, 128.89, 128.95, 129.08, 129.41, 129.90, 130.11,
130.26, 130.48, 130.76, 130.93, 131.03, 131.08, 134.31, 134.47, 134.98, 137.32, 137.53, 138.06, 138.28,
138.48, 146.85, 148.09, 148.45. HRMS (m/z): Calcd. for C28H21ClN2: 420.1393. Found: 420.1399 (M+).
4-(4,5-Diphenyl-1-(4-methylphenyl)-1H-imidazol-2-yl)-2-ethoxyphenol (6): Yield: 94%. m.p.: 180–182 °C;
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IR (KBr, cm−1): 2956, 1613, 1560, 1416, 1139. H-NMR (500 MHz, DMSO-d6) δH: 1.32 (t, 3H,
J = 7.6 Hz), 2.30 (s, 3H), 3.90 (q, 2H, J = 7.6 Hz), 6.84 (d, 1H, J = 7.6 Hz), 6.75 (s, 1H), 6.91 (d, 2H,
J = 7.6 Hz), 7.00–7.06 (m, 3H), 7.10–7.25 (m, 6H), 7.58 (d, 2H, J = 7.6 Hz), 7.97 (d, 2H, J = 7.6 Hz).
13C-NMR (125 MHz, DMSO) δC: 14.89, 21.23, 31.06, 64.42, 112.70, 114.13, 122.46, 122.79, 126.60,
127.53, 127.93, 128.23, 128.35, 128.41, 129.16, 129.79, 130.03, 130.65, 130.94, 131.26, 133.10, 134.66,
134.84, 135.03, 137.92, 138.20, 145.41, 146.13, 147.14, 194.72, 207.16. HRMS (m/z): Calcd. for
C30H26N2O2: 446.1994. Found: 446.1981 (M+).
2-(4-Ethylphenyl)-4,5-diphenyl-1-(4-methylphenyl)-1H-imidazole (7): Yield: 93%. m.p.: 212–214 °C;
IR (KBr, cm−1): 2967, 1694, 1523, 1461, 1245. 1H-NMR (400 MHz, CDCl3) δH: 1.19 (s, 3H), 2.31 (s, 3H),
2.61 (m, 2H), 6.90 (d, J = 7 Hz, 1H), 7.00 (d, J = 8.2 Hz, 2H), 7.15–7.42 (m, 6H), 7.52 (d, J = 7.4 Hz,
2H), 7.58 (d, J = 7.4 Hz, 2H), 7.65 (t, J = 8 Hz, 2H), 8.00 (d, J = 8 Hz, 2H). 13C-NMR (100 MHz, CDCl3)
δC: 15.36, 21.31, 28.70, 31.06, 125.47, 126.59, 127.53, 127.70, 127.92, 127.98, 128.11, 128.23, 128.27,
128.40, 128.45, 128.68, 128.95, 129.16, 129.78, 130.04, 130.84, 130.99, 131.27, 133.11, 134.72, 135.04,
138.17, 144.43, 147.24. HRMS (m/z): Calcd. for C30H26N2: 414.2096. Found: 414.2090 (M+).
4-(4,5-Diphenyl-1-(4-methylphenyl)-1H-imidazol-2-yl)phenol (8): Yield: 94%. m.p.: >280 °C; IR
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(KBr, cm−1): 2956, 1619, 1562, 1414, 1287. H-NMR (400 MHz, CDCl3) δH: 2.26 (s, 3H), 6.65 (d,
J = 7.4 Hz, 2H), 7.08–7.24 (m, 7H), 7.32 (d, J = 7.4 Hz, 3H), 7.49 (d, J = 7.4 Hz, 2H), 7.68 (t, J = 7.2 Hz,
2H), 7.81 (t, J = 7 Hz, 3H), 7.95 (d, J = 5.6 Hz, 2H). 13C-NMR (100 MHz, CDCl3) δC: 21.09, 115.40,
121.86, 126.69, 126.77, 128.53, 128.71, 128.87, 128.93, 129.97, 130.01, 130.05, 130.23, 131.08,
131.20, 131.60, 132.74, 134.79, 135.12, 135.99, 136.83, 138.33, 158.01. HRMS (m/z): Calcd. for
C28H22N2O: 402.1732. Found: 402.1720 (M+).
2-(3,5-Dimethoxyphenyl)-4,5-diphenyl-1-(4-methylphenyl)-1H-imidazole (9): Yield: 94%. m.p.: 140–142 °C;
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IR (KBr, cm−1): 2923, 1609, 1567, 1495, 1165. H-NMR (400 MHz, CDCl3) δH: 2.20 (s, 3H), 3.60 (s,
6H), 5.55 (d, 1H), 6.71 (d, J = 7.2 Hz, 2H), 6.95 (d, J = 7.2 Hz, 2H), 7.22 (d, J = 7.4 Hz, 2H), 7.40–7.60
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(m, 6H), 7.97 (d, J = 7.2 Hz, 4H). C-NMR (100 MHz, CDCl3) δC: 29.83, 56.14, 106.16, 126.70,
127.56, 128.02, 128.28, 128.46, 128.49, 129.17, 129.83, 130.06, 130.86, 131.28, 133.14, 135.03, 138.02,
138.32, 146.63, 147.04. HRMS (m/z): Calcd. for C30H26N2O2: 446.1994. Found: 446.1980 (M+).
4,5-Diphenyl-1-(4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-1H-imidazole (10): Yield: 93%. m.p.:
102–104 °C; IR (KBr, cm−1): 2934, 1693, 1567, 1436, 1173. 1H-NMR (400 MHz, CDCl3) δH: 2.30 (s,
3H), 3.61 (s, 6H), 3.81 (s, 3H), 6.70 (s, 3H), 6.90 (d, J = 8 Hz, 3H), 7.10 (d, J = 8 Hz, 2H), 7.30–7.50