36 G.H. Mahdavinia et al.
2-(4-Methylphenyl)-5-nitrobenzimidazole
(3k) mp
211–
References
213°C; yield 88%; reaction time 25 min; IR: νmax 3435, 1637 cm-1;
1H NMR: δ 13.53 (s, 1H), 7.39 (d, J=9.0 Hz, 2H), 6.54 (d, J=12.0
Hz, 1H), 6.04 (s, 2H), 5.06 (s, 2H), 2.39 (s, 3H); 13C NMR: δ 21.1,
108.0, 111.4, 115.6, 126.8, 127.0, 129.8, 134.0, 136.8, 142.1, 143.4,
153.1; MS (EI, 70 eV): m/z (%) 253 (80) [M+], 153 (100), 107 (43),
80 (59).
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2-(4-Nitrophenyl)-5-nitrobenzimidazole (3l) mp 222–224°C;
yield 98%; reaction time 5 min; IR: νmax 3486, 3388, 3101, 1612
1
cm-1; H NMR: δ 13.49 (s, 1H), 9.07 (s, 1H), 8.98 (s, 1H), 8.11 (s,
1H), 7.94 (d, J=9.0 Hz, 1H), 6.91 (s, 2H), 6.78 (d, J=9.0 Hz, 1H);
13C NMR: δ 113.3, 122.3, 123.8, 125.1, 130.1, 132.7, 135.9, 141.7,
148.8, 151.5, 157.4; MS (EI, 70 eV): m/z (%) 284 (70) [M+], 254
(95), 200 (42), 164 (100), 118 (81).
2-(4-Bromophenyl)benzimidazole-5-carboxylic acid (3m) m p
183–185°C; yield 85%; reaction time 40 min; IR: 3379, 3091, 1678,
1
1635 cm-1; H NMR: δ 13.49 (s, 1H), 12.76 (s, 1H), 8.18 (s, 1H),
8.14 (d, J=8.0 Hz, 2H), 7.84 (d, J=8.0 Hz, 1H), 7.79 (d, J=8.0 Hz,
2H), 7.66 (d, J=8.0 Hz, 1H); 13C NMR: δ 123.2, 123.9, 124.8, 128.6,
128.8, 132.1, 139.2, 141.7, 147.0, 148.7, 152.0, 167.8; MS (EI, 70
eV): m/z (%) 316 (100) [M+], 229 (40), 273 (12), 271 (13), 192 (18).
2-(4-Chlorophenyl)benzimidazole-5-carboxylic acid (3n) mp
168–169°C; yield 80%; reaction time 35 min; IR: 1622, 1683, 3101,
Brain, C. T.; Brunton, S. A. An intramolecular palladium-catalysed
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1
3414 cm-1; H NMR: δ 13.29 (s, 1H), 12.76 (s, 1H), 8.20 (d, J=8.5
Hz, 3H), 7.84 (m, CH), 7.64 (d, J=8.5 Hz, 3H); 13C NMR: δ 123.7,
128.4, 128.5, 129.2, 135.1, 139.1, 140.7, 142.1, 143.3, 147.1, 156.6,
167.8; MS (EI, 70 eV): m/z (%) 272 (100) [M+], 227 (17), 176 (23).
Anal. Calcd for C14H9ClN2O2: C, 61.66; H, 3.33; N, 10.27. Found:
C, 61.44; H, 3.04; N, 10.43.
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2-(4-Cyanophenyl)benzimidazole-5-carboxylic acid (3o) mp
183–185°C; yield 90%; reaction time 35 min; IR: 1606, 2228, 3368
cm-1; 1H NMR: δ 13.48 (s, 1H), 12.65 (s, 1H), 8.85 (s, 1H), 8.36 (d,
J=8.4 Hz, 1H), 8.03 (d, J=8.4 Hz, 1H), 7.86 (d, J=8.4 Hz, 2H), 7.70
(d, J=8.4 Hz, 1H); 13C NMR: δ 112.4, 113.7, 117.3, 118.7, 127.3,
129.3, 132.6, 133.0, 133.7, 140.4, 149.0, 155.4, 167.7; MS (EI, 70
eV): m/z (%) 263 (100) [M+], 246 (49), 218 (18), 116 (15). Anal.
Calcd for C15H9N3O2: C, 68.44; H, 3.45; N, 15.96. Found: C, 67.84;
H, 3.14; N, 15.75.
2-(4-Methylphenyl)benzimidazole-5-carboxylic acid (3p) mp
200–205°C; yield 60%; reaction time 45 min; IR: 1628, 1689, 3369,
3426 cm-1; 1H NMR: δ 12.70 (br s, 2H), 8.16 (s, 1H), 8.08 (d, J=6.0
Hz, 2H), 7.82 (d, J=8.0 Hz, 1H), 7.63 (d, J=8.0 Hz, 1H), 7.53 (d,
J=8.0 Hz, 1H), 7.36 (d, J=6.0 Hz, 2H), 2.37 (m, 3H); 13C NMR: δ
21.0, 118.6, 123.5, 124.4, 126.7, 126.8, 129.6, 132.3, 133.1, 140.3,
146.1, 153.7, 167.9 ppm; MS (EI, 70 eV): m/z (%) 252 (100) [M+],
235 (49), 207 (15); Anal. Calcd for C15H12N2O2: C, 71.42; H, 4.79;
N, 11.10. Found: C, 72.03; H, 4.67; N, 10.93.
Feng, X.; Fryxell, G. E.; Wang, L. Q.; Kim, A. Y.; Liu, J.; Kemner, K.
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Thermal and mechanical stability of micelle-templated silica
supports for catalysis. Catal. Today 2001, 68, 191–200.
Gusev, V.Y.; Feng, X.; Bu, Z.; Haller, G. L.; O’Brien, J.A. Mechanical
stability of pure silica mesoporous MCM-41 by nitrogen adsorp-
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2-(4-Nitrophenyl)benzimidazole-5-carboxylic acid (3q) mp
270–272°C; yield 80%; reaction time 30 min; IR: 1602, 1671, 3394,
3501 cm-1; 1H NMR: δ 13.62 (br s), 12.50 (s, 1H), 8.92 (s, 1H),
8.44 (m, 3H), 8.15 (d, J=8.0 Hz, 1H), 7.88 (d, J=7.6 Hz, 1H), 7.61
(d, J=8.0 Hz, 1H); 13C NMR: δ 113.8, 117.3, 118.5, 123.8, 124.3,
127.8, 129.7, 133.0, 142.2, 149.0, 154.9, 167.5; MS (EI, 70 eV): m/z
(%) 283 (100) [M+], 253 (19), 237 (38), 192 (33). Anal. Calcd for
C14H9N3O4: C, 59.37; H, 3.20; N, 14.84. Found: C, 60.08; H, 3.32;
N, 15.03.
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