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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)