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Table 1 Physicochemical characteristic of the synthesized compounds

From: Synthesis and biological profile of substituted benzimidazoles

Comp. Molecular structures with stereochemistry M. formula and CHN analyses M. wt. Rf value % Yield M. Pt. (°C)
1 (E)-N-((E)-3-(4-(Dimethylamino)phenyl) allylidene)-1H-benzo[d]imidazol-2-amine C18H18N4: Anal calcd: C, 74.46; H, 6.25; N, 19.30; Found: C, 74.43; H, 6.27; N, 19.33 290.40 0.76a 76 228–230
2 (E)-1-(((1H-Benzo[d]imidazol-2-yl)imino)methyl)naphthalen-2-ol C18H13N3O: Anal calcd: C, 75.25; H, 4.56; N, 14.63; Found: C, 75.27; H, 4.59; N, 14.60 287.34 0.79a 74 255–257
3 (E)-N-(3,4-Dimethoxybenzylidene)-1H-benzo[d]imidazol-2-amine C16H15N3O2: Anal calcd: C, 68.31; H, 5.37; N, 14.94; Found: C, 68.34; H, 5.35; N, 14.97 281.34 0.77a 78 225–227
4 (E)-4-(((1H-Benzo[d]imidazol-2-yl)imino)methyl)phenol C14H11N3O: Anal calcd: C, 70.87; H, 4.67; Cl, 17.71; Found: C, 70.88; H, 4.65; Cl, 17.73 237.28 0.75a 67 220–222
5 (E)-N-(4-Nitrobenzylidene)-1H-benzo[d]imidazol-2-amine C14H10N4O2: Anal calcd: C, 63.15; H, 3.79; N, 21.04; Found: C, 63.13; H, 3.77; N, 21.07 266.28 0.72a 72 236–238
6 (E)-N-(4-(Dimethylamino)benzylidene)-1H-benzo[d]imidazol-2-amine C16H16N4: Anal calcd: C, 72.70; H, 6.10; N, 21.20; Found: C, 72.73; H, 6.12; N, 21.22 264.36 0.79a 82 238–240
7 (E)-N-(3-Nitrobenzylidene)-1H-benzo[d]imidazol-2-amine C14H10N4O2: Anal calcd: C, 63.15; H, 3.79; N, 21.04; Found: C, 63.18; H, 3.77; N, 21.05 266.28 0.76a 76 190–192
8 (E)-N-Ethylidene-1H-benzo [d]imidazol-2-amine C9H9N3: Anal calcd: C, 67.90; H, 5.70; N, 26.40; Found: C, 67.88; H, 5.72; N, 26.42 159.21 0.72a 80 172–175
9 (E)-N-(4-Methoxybenzylidene)-1H-benzo[d]imidazol-2-amine C15H13N3O: Anal calcd: C, 71.70; H, 5.21; N, 16.72; Found: C, 71.73; H, 5.22; N, 16.74 251.31 0.71a 75 198–200
10 (E)-5-((1H-Benzo[d]imidazol-2-yl)imino)pentanal C12H13N3O: Anal calcd: C, 66.96; H, 6.09; N, 19.52; Found: C, 66.94; H, 6.11; N, 19.55 215.28 0.75a 78 265–267
11 (E)-N-(3,4,5-Trimethoxybenzylidene)-1H-benzo[d]imidazol-2-amine C17H17N3O3: Anal calcd: C, 65.58; H, 5.50; N, 13.50; Found: C, 65.61; H, 5.53; N, 13.52 311.37 0.72a 84 242–245
12 (E)-1-(2-(Ethylideneamino)-1H-benzo[d]imidazol-1-yl)ethanone C11H11N3O: Anal calcd: C, 65.66; H, 5.51; N, 20.88; Found: C, 65.65; H, 5.54; N, 20.86 201.22 0.63b 74 262–265
13 (E)-(3,5-Dinitrophenyl)(2-((4-methoxy-benzylidene)amino)-1H-benzo[d]imidazol-1-yl)methanone C22H15N5O6: Anal calcd: C, 59.33; H, 3.39; N, 15.72; Found: C, 59.35; H, 3.42; N, 15.75 445.38 0.58b 68 243–245
14 (E)-5-((1-(3,5-Dinitrobenzoyl)-1H-benzo[d]imidazol-2-yl)imino)pentanal C14H11N3O2: Anal calcd: C, 55.75; H, 3.69; N, 17.11; Found: C, 55.78; H, 3.71; N, 17.14 253.26 0.66b 65 162–164
15 (E)-5-((1-Acetyl-1H-benzo[d]imidazol-2-yl)imino)pentanal C14H15N3O2: Anal calcd: C, 65.35; H, 5.88; N, 16.33; Found: C, 65.37; H, 5.90; N, 16.36 257.29 0.62b 72 226–228
16 (E)-(3,5-Dinitrophenyl)(2-((4-hydroxybenzylidene)amino)-1H-benzo[d]imidazol-1-yl)methanone C21H13N5O6: Anal calcd: C, 58.47; H, 3.04; N, 16.24; Found: C, 58.49; H, 3.05; N, 16.25 431.36 0.64b 70 175–177
17 (E)-(2-((2,4-Dimethoxybenzylidene)amino) -1H-benzo[d]imidazol-1-yl)(naphthalen-2-yl)methanone C27H21N3O3: Anal calcd: C, 74.47; H, 4.86; N, 9.65; Found: C, 74.49; H, 4.88; N, 9.68 435.47 0.54b 67 120–122
18 (E)-Naphthalen-2-yl(2-((3,4,5-trimethoxybenzylidene)amino)-1H-benzo[d]imidazol-1-yl)methanone C28H23N3O4: Anal calcd: C, 72.24; H, 4.98; N, 9.03; Found: C, 72.27; H, 4.95; N, 9.05 465.5 0.65b 75 210–212
19 (E)-(3,5-Dinitrophenyl)(2-((3,4,5-trimethoxybenzylidene)amino)-1H-benzo[d]imidazol-1-yl)methanone C24H19N5O8: Anal calcd: C, 57.03; H, 3.79; N, 13.86; Found: C, 57.07; H, 3.76; N, 13.88 505.44 0.66b 66 141–143
20 (E)-1-(2-((3,4,5-trimethoxybenzylidene)amino)-1H-benzo[d]imidazol-1-yl)hexadecan-1-one C33H47N3O4: Anal calcd: C, 72.10; H, 8.62; N, 7.64; Found: C, 72.11; H, 8.65; N, 7.67 549.74 0.62b 78 136–138
21 (E)-(3-Nitrophenyl)(2-((4-(pyridin-2-yl)benzylidene)amino)-1H-benzo[d]imidazol-1-yl)methanone C26H17N5O3: Anal calcd: C, 69.79; H, 3.83; N, 15.65; Found: C, 69.77; H, 3.86; N, 15.68 447.44 0.57b 67 142–144
22 (2-((E)-((E)-3-(4-(Dimethylamino)phenyl) allylidene)amino)-1H-benzo[d]imidazol-1-yl)(3-nitrophenyl)methanone C25H21N5O3: Anal calcd: C, 68.33; H, 4.82; N, 15.94; Found: C, 68.37; H, 4.80; N, 15.97 439.47 0.59b 82 126–128
23 (E)-(2-((4-(Dimethylamino)benzylidene) amino)-1H-benzo[d]imidazol-1-yl)(3-nitrophenyl)methanone C23H19N5O3: Anal calcd: C, 66.82; H, 4.63; N, 16.94; Found: C, 66.83; H, 4.66; N, 16.97 413.43 0.63b 76 131–133
24 (E)-(2-(((2-hydroxynaphthalen-1-yl)-methylene)amino)-1H-benzo[d]imidazol-1-yl)(3-nitrophenyl)methanone C25H16N4O4: Anal calcd: C, 68.80; H, 3.70; N, 12.84; Found: C, 68.83; H, 3.72; N, 12.87 436.42 0.64b 65 134–136
25 (E)-(2-((4-Nitrobenzylidene)amino)-1H-benzo[d]imidazol-1-yl)(3-nitrophenyl) methanone C21H13N5O5: Anal calcd: C, 60.72; H, 3.15; N, 16.86; Found: C, 60.75; H, 3.17; N, 16.89 415.36 0.66b 74 119–121
26 (E)-Naphthalen-2-yl(2-((4-nitrobenzylidene)amino)-1H-benzo[d]imidazol-1-yl)methanone C25H16N4O3: Anal calcd: C, 71.42; H, 3.84; N, 13.33; Found: C, 71.43; H, 3.87; N, 13.37 420.42 0.52b 62 176–178
27 (E)-(2-((3,4-Dimethoxybenzylidene)amino) -1H-benzo[d]imidazol-1-yl)(3-nitro phenyl)methanone C23H18N4O5: Anal calcd: C, 64.18; H, 4.22; N, 13.02; Found: C, 64.21; H, 4.25; N, 13.04 430.41 0.63b 65 235–237
28 (E)-1-(2-((4-Nitrobenzylidene)amino)-1H-benzo[d]imidazol-1-yl)hexadecan-1-one C30H40N4O3: Anal calcd: C, 71.40; H, 7.99; N, 11.10; Found: C, 71.39; H, 7.97; N, 11.12 504.66 0.59b 66 126–128
29 (E)-1-(2-((4-(Dimethylamino)benzylidene) amino)-1H-benzo[d]imidazol-1-yl)hexadecan-1-one C34H48N4O: Anal calcd: C, 77.23; H, 9.15; N, 10.60; Found: C, 77.21; H, 9.16; N, 10.63 528.77 0.64b 68 131–133
30 (E)-(2-((4-(Dimethylamino)benzylidene) amino)-1H-benzo[d]imidazol-1-yl)(naphthalen-2-yl)methanone C27H22N4O: Anal calcd: C, 77.49; H, 5.30; N, 13.39; Found: C, 77.51; H, 5.32; N, 13.42 418.49 0.62b 76 192–195
  1. TLC mobile phase: a Ethyl acetate: Methanol (7:3); b Chloroform: Methanol (8:2)