2990
M. LEI, L. MA, AND L. HU
2-Phenyl-1H-benzimidazole (3a). Yield: 93%; white solid; mp 294 ꢀC (lit.[11]
1
295 ꢀC). H NMR (400 MHz, DMSO-d6): d ¼ 12.93 (brs, 1 H), 8.19 (d, J ¼ 7.2 Hz,
2 H), 7.44–7.65 (m, 5 H), 7.21 (m, 2 H). MS (EI, 70 eV): m=z (%) ¼ 193 (Mþ).
2-(4-Methyl-phenyl)-1H-benzimidazole (3b). Yield: 91%; white solid; mp
278 ꢀC (lit.[11] 277 ꢀC). MS (EI, 70 eV): m=z (%) ¼ 207 (Mþ).
2-(4-Methoxy-phenyl)-1H-benzimidazole (3c). Yield:þ93%; white solid; mp
225 ꢀC (lit.[11] 223–226 ꢀC). MS (EI, 70 eV): m=z (%) ¼ 223 (M ).
2-(4-Hydroxyl-phenyl)-1H-benzimidazole (3d). Yield: 92%; white solid;
1
mp 278 ꢀC. H NMR (400 MHz, DMSO-d6): d ¼ 12.67 (brs, 1 H), 10.01 (brs, 1 H),
8.04 (d, J ¼ 7.2 Hz, 2 H), 7.55 (m, 2 H), 7.16 (m, 2 H), 6.95 (d, J ¼ 7.2 Hz, 2 H).
MS (ESI): m=z ¼ 210 ([M þ 1]þ).
2-(4-Chlorophenyl)-1H-benzimidazole (3e). Yield: 92%; white solid; mp
1
292 ꢀC (lit.[17d] 294 ꢀC). H NMR (400 MHz, DMSO-d6): d ¼ 13.00 (brs, 1 H), 8.21
(d, J ¼ 8.4 Hz, 2 H), 7.69 (d, J ¼ 6.4 Hz, 1 H), 7.64 (d, J ¼ 8.4 Hz, 2 H), 7.55 (d,
J ¼ 6.4 Hz, 1 H), 7.23 (m, 2 H). MS (EI, 70 eV): m=z ¼ 227 (Mþ).
2-(3-Nitrophenyl)-1H-benzimidazole (3f). Yield:þ92%; yellow solid; mp
205 ꢀC (lit.[10] 204–206 ꢀC). MS (EI, 70 eV): m=z ¼ 238 (M ).
1-Benzyl-2-phenyl-1H-benzimidazole (4a). Yield: 91%; white solid; mp
1
134 ꢀC (lit.[12] 133–134 ꢀC). H NMR (400 MHz, CDCl3): d ¼ 7.81 (d, J ¼ 8.0 Hz, 1
H), 7.60 (dd, J ¼ 8.0 and 2.0 Hz, 2 H), 7.31–7.40 (m, 3 H), 7.18–7.25 (m, 5 H),
7.04–7.07 (m, 3 H), 5.41 (s, 2 H). MS (EI, 70 eV): m=z ¼ 284 (Mþ).
1-(4-Methylbenzyl)-2-(4-methylphenyl)-1H-benzimidazole (4b). Yield:
90%; white solid; mp 131 ꢀC (lit.[12] 128–129 ꢀC). 1H NMR (400 MHz, CDCl3):
d ¼ 7.83 (m, 1 H), 7.57 (d, J ¼ 8.0 Hz, 2 H), 7.28 (m, 1 H), 7.25 (d, J ¼ 8.0 Hz, 2
H), 7.20 (m, 2 H), 7.13 (d, J ¼ 8.0 Hz, 2 H), 6.97 (d, J ¼ 8.0 Hz, 2 H), 5.38 (s, 2
H), 2.39 (s, 3 H), 2.33 (s, 3 H). MS (EI, 70 eV): m=z ¼ 312 (Mþ).
1-(4-Methoxybenzyl)-2-(4-methoxyphenyl)-1H-benzimidazole
1
(4c). Yield: 92%; white solid; mp 130 ꢀC (lit.[12] 127–129 ꢀC). H NMR (400 MHz,
CDCl3): d ¼ 7.83 (d, J ¼ 8.0 Hz, 1 H), 7.61 (d, J ¼ 8.8 Hz, 2 H), 7.20–7.30 (m, 3
H), 7.02 (d, J ¼ 8.8 Hz, 2 H), 6.95 (d, J ¼ 8.8 Hz, 2 H), 6.84 (d, J ¼ 8.0 Hz, 2 H),
5.38 (s, 2 H), 3.78 (s, 3 H), 3.84 (s, 3 H). MS (EI, 70 eV): m=z ¼ 344 (Mþ).
1-(3,4-Dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)-1H-1,3-
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benzimidazole (4d). Yield: 93%; white solid; mp 173 ꢀC (lit.[20] 171–173 ꢀC). H
NMR (400 MHz, CDCl3): d ¼ 7.80–7.90 (m, 1 H), 7.53–7.57 (m, 1 H), 7.22–7.31
(m, 4 H), 6.94 (d, J ¼ 8.4 Hz, 1 H), 6.80 (d, J ¼ 8.4 Hz, 1 H), 6.60–6.70 (m, 2 H),
5.42 (s, 2 H), 3.92 (s, 3 H), 3.84 (s, 3 H), 3.78 (s, 3 H), 3.75 (s, 3 H). MS
(EI, 70 eV): m=z ¼ 404 (Mþ).
1-(4-Hydroxybenzyl)-2-(4-hydroxyphenyl)-1H-benzimidazole
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(4e). Yield: 90%; white solid; mp 116 ꢀC (lit.[21] 111–113 ꢀC). H NMR (400 MHz,
CDCl3): d ¼ 7.75 (d, J ¼ 8.0 Hz, 2 H), 7.19–7.22 (m, 4 H), 7.03–7.08 (m, 3 H),
6.87–6.90 (m, 3 H), 5.25 (s, 2 H). MS (ESI): m=z ¼ 317 ([M þ 1]þ).