General Procedure for the Synthesis of 2,4,5-Trisubstituted Imidazoles 1a–k. A mixture of benzil (10 mmol,
2.143 g), aldehyde (10 mmol), NH OAc (30 mmol, 2.336 g), and AcOH (10 mmol, 0.601 g) was stirred and refluxed in
4
10 mL ethanol for the appropriate time mentioned in Table 1. After completion of reaction (monitored by TLC), the mixture
was cooled to room temperature and the product precipitated from solution. The resulting solid was filtered under suction and
washed thoroughly with EtOH to give the pure product (single spot on TLC). All the products (1a–k) were fully characterized
1
by mp, IR, H NMR, and mass spectroscopic and elemental analysis. They have been identified by comparison with reported
spectral data. Spectral data for new compound are as follows.
–1
2-(2-Nitrophenyl)-4,5-diphenylimidazole (1h). Yellow solid. IR (KBr, ꢁ, cm ): 3458 (NH), 1584 (C=N), 1507
1
(C=C), 1481 (C=C), 1525 (NO ), 1352 (ꢁ ), 852 (Ar-H), 777 (Ar-H), 694 (Ar-H). H NMR spectrum (300 MHz, DMSO-d ,
2
C-N
6
ꢂ, ppm, J/Hz): 7.23–7.52 (10H, m, 2C H ), 7.61–7.66 (1H, t, J = 7.5, C H ), 7.76–7.81 (1H, t, J = 7.5, C H ), 7.92–7.94 (1H,
6
5
6
4
6 4
+
d, J = 7.8, C H ), 7.99–8.01 (1H, d, J = 7.5, C H ), 12.97 (1H, s, NH). ESI-MS m/z 342 (M + 1) ; C H N O (341.4).
6
4
6
4
21 15 3 2
General Procedure for the Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles 2a–p. A mixture of benzil (10 mmol,
2.143 g), aldehyde (10 mmol), amine (10 mmol), NH OAc (30 mmol, 2.336 g), and AcOH (10 mmol, 0.601 g) was stirred and
4
refluxed in 10 mL ethanol for 3 h. After completion of reaction (monitored by TLC), the same workup was followed as shown
in the synthesis of 2,4,5-trisubstituted imidazoles 1a–k.
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