Med Chem Res (2014) 23:1290–1299
1297
nucleus), 1688 (–C=O str.), 2856 (–CH2 str. methylene),
2926 (–CH str. methoxy group), 3099 (–CH str. aromatic
DMSO-d6, d, ppm): 39.4 (C8), 103.2 (C14), 112.2 (C12),
115.2 (C2), 115.2 (C4), 117.1 (C11), 121.7 (C5), 121.7 (C1),
139.0 (C15), 141.7 (C6), 147.8 (C9), 157.2 (C13), 159.1
(C3), 167.3 (C7); MS (m/z): 344 (M?). For C17H17N3O3S:
C, 59.46; H, 4.99; N, 12.24; S, 9.34 %. Found: C, 59.50; H,
5.04; N, 12.27; S, 9.38 %.
1
ring), 3391 (–NH str. sec. amine); H NMR (400 MHz,
DMSO-d6, d, ppm): 3.69 (3H, s, –OCH3), 4.22 (2H, s,
–CH2), 6.56–8.03 (7H, m, Ar–H), 11.23 (1H, s, –NH),
12.37 (1H, s, benzimidazole-NH); 13C NMR (100 MHz,
DMSO-d6, d, ppm): 39.4 (C8), 103.2 (C14), 112.2 (C12),
115.2 (C4), 115.2 (C2), 117.1 (C11), 121.7 (C5), 121.7 (C1),
139.0 (C15), 141.7 (C6), 147.8 (C9), 157.2 (C13), 163.2(C3),
167.3 (C7); MS (m/z): 332 (M?). For C16H14N3O2FS: C,
57.99; H, 4.26; N, 12.68; S, 9.68 %. Found: C, 58.02; H,
4.30; N, 12.72; S, 9.71 %.
2-(5-Methoxy-1H-benzo[d]imidazol-2-ylthio)-N-(2-nitro-
phenyl)acetamide III10 Solid yellow; yield: 60 %; m.p.:
105 °C; IR (ATR, cm-1): 1582 (–C=N str. benzimidazole
nucleus), 1693 (–C=O str.), 2848 (–CH2 str. methylene),
2925 (–CH str. methoxy group), 3098 (–CH str. aromatic
1
ring), 3388 (–NH str. sec. amine); H NMR (400 MHz,
2-(5-Methoxy-1H-benzo[d]imidazol-2-ylthio)-N-(2-methoxy-
phenyl)acetamide III7 Solid cream; yield: 44 %; m.p.:
156 °C; IR (ATR, cm-1): 1586 (–C=N str. benzimidazole
nucleus), 1690 (–C=O str.), 2859 (–CH2 str. methylene),
2920 (–CH str. methoxy group), 3087 (–CH str. aromatic
DMSO-d6, d, ppm): 3.75 (3H, s, –OCH3), 4.18 (2H, s,
–CH2), 6.70–8.19 (7H, m, Ar–H), 11.15 (1H, s, –NH),
12.27 (1H, s, benzimidazole-NH); 13C NMR (100 MHz,
DMSO-d6, d, ppm): 39.4 (C8), 103.2 (C14), 112.2 (C12),
117.1 (C11), 115.0 (C5), 118.0 (C3), 126.0 (C2), 131.9 (C1),
135.8 (C4), 139.0 (C15), 145.2 (C6), 147.8 (C9), 157.2
(C13), 167.3 (C7); MS (m/z): 359 (M?). For C16H16N4O4S:
C, 53.62; H, 3.94; N, 15.63; S, 8.95 %. Found: C, 53.66; H,
3.95; N, 15.66; S, 8.99 %.
1
ring), 3402 (–NH str. sec. amine); H NMR (400 MHz,
DMSO-d6, d, ppm): 3.72 (3H, s, –OCH3), 4.17 (2H, s,
–CH2), 6.71–8.06 (7H, m, Ar–H), 11.14 (1H, s, –NH),
12.37 (1H, s, benzimidazole-NH); 13C NMR (100 MHz,
DMSO-d6, d, ppm): 39.4 (C8), 103.2 (C14), 112.2 (C12),
117.1 (C11), 120.5 (C5), 149.6 (C1), 128.5(C3), 124.5 (C4),
113.0 (C2), 139.0 (C15), 126.9 (C6), 147.8 (C9), 157.2
(C13), 167.3 (C7); MS (m/z): 344 (M?). For C17H17N3O3S:
C, 59.46; H, 4.99; N, 12.24; S, 9.34 %. Found: C, 59.51; H,
5.04; N, 12.28; S, 9.39 %.
2-(5-Methoxy-1H-benzo[d]imidazol-2-ylthio)-N-o-tolylac-
etamide III11 Solid light brown; yield: 53 %; m.p.:
156 °C; IR (ATR, cm-1): 1576 (–C=N str. benzimidazole
nucleus), 1687 (–C=O str.), 2856 (–CH2 str. methylene),
2918 (–CH str. methoxy group), 3091 (–CH str. aromatic
1
ring), 3397 (–NH str. sec. amine); H NMR (400 MHz,
2-(5-Methoxy-1H-benzo[d]imidazol-2-ylthio)-N-m-tolylac-
etamide III8 Solid white; yield: 54 %; m.p.: 105 °C; IR
(ATR, cm-1): 1576 (–C=N str. benzimidazole nucleus),
1691 (–C=O str.), 2852 (–CH2 str. methylene), 2944 (–CH
str. methoxy group), 3092 (–CH str. aromatic ring), 3396
DMSO-d6, d, ppm): 2.53 (3H, s, –CH3); 3.76 (3H, s,
–OCH3), 4.14 (2H, s, –CH2), 6.80–8.21 (7H, m, Ar–H),
11.27 (1H, s, –NH), 12.33 (1H, s, benzimidazole-NH); 13
C
NMR (100 MHz, DMSO-d6, d, ppm): 39.4 (C8), 103.2
(C14), 112.2 (C12), 117.1 (C11), 125.2 (C5), 126.0 (C4),
129.5(C3), 130.8 (C2), 132.0 (C1), 137.7 (C6), 139.0 (C15),
147.8 (C9), 157.2 (C13), 167.3 (C7); MS (m/z): 328 (M?).
For C17H17N3O2S: C, 62.36; H, 5.23; N, 12.83; S, 7.79 %.
Found: C, 62.41; H, 5.26; N, 12.87; S, 7.74 %.
1
(–NH str. sec. amine); H NMR (400 MHz, DMSO-d6, d,
ppm): 3.69 (3H, s, –OCH3), 4.22 (2H, s, –CH2), 6.66–8.02
(7H, m, Ar–H), 11.21 (1H, s, –NH), 12.32 (1H, s, benz-
imidazole-NH); 13C NMR (100 MHz, DMSO-d6, d, ppm):
39.4 (C8), 103.2 (C14), 112.2 (C12), 117.1 (C11), 119.2 (C5),
121.7 (C1), 124.5(C3), 128.8 (C4), 136.6 (C2), 139.0 (C15),
141.7 (C6), 147.8 (C9), 157.2 (C13), 167.3 (C7); MS (m/z):
328 (M?). For C17H17N3O2S: C, 62.36; H, 5.23; N, 12.83;
S, 9.79 %. Found: C, 62.41; H, 5.28; N, 12.87; S, 9.84 %.
2-(5-Methoxy-1H-benzo[d]imidazol-2-ylthio)-N-p-tolylac-
etamide III12 Solid light brown; yield: 76 %; m.p.:
175 °C; IR (ATR, cm-1): 1584 (–C=N str. benzimidazole
nucleus), 1692 (–C=O str.), 2848 (–CH2 str. methylene),
2926 (–CH str. methoxy group), 3088 (–CH str. aromatic
2-(5-Methoxy-1H-benzo[d]imidazol-2-ylthio)-N-(4-methoxy-
phenyl)acetamide III9 Solid off-white; yield: 62 %; m.p.:
195 °C; IR (ATR, cm-1): 1587 (–C=N str. benzimidazole
nucleus), 1698 (–C=O str.), 2846 (–CH2 str. methylene),
2936 (–CH str. methoxy group), 3086 (–CH str. aromatic
1
ring), 3387 (–NH str. sec. amine); H NMR (400 MHz,
DMSO-d6, d, ppm): 2.49 (3H, s, –CH3); 3.79 (3H, s,
–OCH3), 4.20 (2H, s, –CH2), 6.96–8.12 (7H, m, Ar–H),
11.17 (1H, s, –NH), 12.30 (1H, s, benzimidazole-NH); 13
C
1
NMR (100 MHz, DMSO-d6, d, ppm): 39.4 (C8), 103.2
(C14), 112.2 (C12), 117.1 (C11), 121.7 (C1), 123.5 (C5),
129.4 (C2), 129.4 (C4), 136.8(C3), 139.0 (C15), 141.7 (C6),
147.8 (C9), 157.2 (C13), 167.3 (C7); MS (m/z): 328 (M?).
ring), 3391 (–NH str. sec. amine); H NMR (400 MHz,
DMSO-d6, d, ppm): 3.80 (3H, s, –OCH3), 4.16 (2H, s,
–CH2), 6.74–8.10 (7H, m, Ar–H), 11.28 (1H, s, –NH),
12.29 (1H, s, benzimidazole-NH); 13C NMR (100 MHz,
123