2-Aryl Benzimidazoles
65
the compounds were characterized by comparing their
physical and spectral data with those of reported com-
300 MHz): d 12.30 (br, 1H, s, –NH), 7.21–8.05 (8H, m);
13C NMR (DMSO-d6, 75 MHz): d 141.8, 130.2, 138.0,
125.1, 120.5, 115.1; EIMS: m/z 210 (M ? H)?; Anal.
Calcd. for C13H10N2O (210): C, 74.27; H, 4.79; N, 13.33.
Found: C, 74.26; H, 4.78; N, 13.32.
1
pounds. The m.p., IR, H NMR, 13C NMR and EIMS data
of all synthesized compounds are given below-
2.4 Product Characterization Data
2.4.6 2-(4-Methylphenyl)-1H-benzimidazole 3f
2.4.1 2-Phenyl-1H-benzimidazole 3a
Light yellow solid: m.p. = 261–263 °C [34]; IR (KBr):
White solid: m.p. = 287–288 °C [33]; IR (KBr): 3334,
3340, 3016, 2854, 1625, 1439, 1288 cm-1 1H NMR
;
3198, 1625, 1510, 1287 cm-1 1H NMR (DMSO-d6,
;
(DMSO-d6, 300 MHz): d 2.24 (3H, s), 12.21 (br, 1H, s,
–NH), 7.12–7.90 (m, 8H); 13C NMR (DMSO-d6, 75 MHz):
d 21.4, 116.8, 122.5, 126.3, 138.0,140.8; EIMS: m/z 208
(M ? H)?; Anal. Calcd. for C14H12N2 (208): C, 80.74; H,
5.81; N, 13.45. Found: C, 80.82; H, 5.78; N, 13.41.
300 MHz): d 12.93 (1H, s, –NH), 7.92 (2H, d, J = 1.3 Hz),
7.47 (m, 1H), 7.22 (4H, m), 6.95 (2H, s); 13C NMR
(DMSO-d6, 75 MHz): d 142.8, 136.1, 135.2, 129.4, 120.2,
114.9; EIMS: m/z 194.0 (M ? H)?; Anal. Calcd. for
C13H10N2 (194): C, 80.39; H, 5.19; N, 14.42. Found: C,
80.35; H, 5.21; N, 14.39.
2.4.7 2-(4-Methoxyphenyl)-1H-benzimidazole 3g
2.4.2 2-(2-Chlorophenyl)-1H-benzimidazoles 3b
Light yellow solid: m.p. = 225–227 °C [33]; IR (KBr):
White solid: m.p. = 231–233 °C [34]; IR (KBr): 3421,
3068, 2886, 1637, 1464, 1245 cm-1; 1H NMR (DMSO-d6,
300 MHz): d 12.21 (br, 1H, s, –NH), 7.25–7.95 (8H, m);
13C NMR (DMSO-d6, 75 MHz): d 145.0, 132.5, 138.2,
120.8, 119.5, 114.1; EIMS: m/z 219.0 (35Cl [M ? H]?);
Anal. Calcd. for C13H9N2Cl (229): C, 68.28; H, 3.97; N,
12.25. Found: C, 68.25; H, 3.99; N, 12.22.
3339, 3000, 2928, 1609, 1440, 1292 cm-1 1H NMR
;
(DMSO-d6, 300 MHz): d 12.70 (1H, s), 8.15 (2H, d,
J = 1.75 Hz), 7.66 (1H, s), 7.42 (1H, s), 7.18 (4H, m), 3.76
(3H, s); 13C NMR (DMSO-d6, 75 MHz): d 56.3, 115.6,
119.1, 121.9, 122.6, 126.7, 127.8, 129.8, 135.3, 139.9,
144.1, 151.7; EIMS: m/z 225 (M ? 1)?; Anal. Calcd. for
C14H12N2O (224): C, 74.98; H, 5.39; N, 12.49. Found: C,
75.00; H, 5.38; N, 12.45.
2.4.3 2-(4-Chlorophenyl)-1H-benzimidazoles 3c
Light yellow solid: m.p. = 291–293 °C [34]; IR (KBr):
3338, 2923, 1624, 1448, 1487 cm-1; 1H NMR (DMSO-d6,
300 MHz): d 12.55 (br, 1H, s, –NH), 8.14 (2H, d,
J = 1.52 Hz), 7.61 (1H, s), 7.23–7.28 (3H, s), 7.12–7.04
(2H, s); 13C NMR (DMSO-d6, 75 MHz): d 142.5, 137.1,
133.9, 129.8, 120.5, 114.1; EIMS: m/z 219.0 (35Cl
[M ? H]?); Anal. Calcd. for C13H9N2Cl (229): C, 68.28;
H, 3.97; N, 12.25. Found: C, 68.29; H, 3.94; N, 12.27.
2.4.8 2-(1H-Benzimdazole-2-yl)-6-methoxy-phenol 3h
(Unknown)
White solid: m.p. = 185–187 °C; IR (KBr): 3360, 2923,
2843, 1612, 1495, 1272 cm-1 1H NMR (DMSO-d6,
;
300 MHz):
d
12.70 (s, 1H), 7.12–7.98 (8H, d,
J = 1.54 Hz), 3.62 (s, 3H); 13C NMR (DMSO-d6,
75 MHz): d 55.2, 115.1, 120.6, 122.8, 125.4, 137.2, 141.2,
149.1; EIMS: m/z 235 (M ? 1)?; Anal. Calcd. for
C14H12N2O2 (240): C, 69.99; H, 5.03; N, 11.66. Found: C,
69.95; H, 5.05; N, 11.62.
2.4.4 2-(1H-Benzimidazole-2-yl)-phenol 3d
White solid: m.p. = 235–237 °C [33]; IR (KBr): 3378,
3459, 2859, 1614, 1495 cm-1 1H NMR (DMSO-d6,
;
2.4.9 4-(1H-Benzimidazole-2-yl)-phenylamine 3i
300 MHz): d 12.48 (br, 1H, s, –NH), 7.18–7.93 (8H, m);
13C NMR (DMSO-d6, 75 MHz): d 21.4, 140.8, 138.0,
126.3, 122.5, 116.8; EIMS: m/z 208 (M ? H)?; Anal.
Calcd. for C13H10N2O (210): C, 74.27; H, 4.79; N, 13.33
Found: C, 74.30; H, 4.75; N, 13.35.
Yellowish white crystals: m.p. = 246–248 °C, lit
m.p. = 248 °C [35]; IR (KBr): 3351, 3062, 2923, 1610,
1491, 1281 cm-1 1H NMR (DMSO-d6, 300 MHz): d
;
12.42 (s, 1H), 6.92–7.75 (d, 8H, J = 1.50 Hz), 4.55 (s,
2H); 13C NMR (DMSO-d6, 75 MHz): d 115.7, 122.1,
126.0, 138.3, 140.9; EIMS: m/z 209 (M ? 1)?; Anal.
Calcd. for C13H11N3 (209): C, 74.62; H, 5.30; N, 20.08.
Found: C, 74.60; H, 5.29; N, 20.10.
2.4.5 4-(1H-Benzimidazole-2-yl)-phenol 3e
Yellow solid: m.p. = 218–220 °C [33]; IR (KBr): 3357,
1609, 1510, 1444, 1247 cm-1 1H NMR (DMSO-d6,
;
123