Med Chem Res (2013) 22:1229–1237
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Ethyl 2-(6-nitro-2-trifluoromethyl)-1H-benzimidazole-
C12H11ClF3N3O2: C, 44.80; H, 3.45; N, 13.66. Found: C,
44.68; H, 3.44; N, 13.65.
1-yl)acetate (3f)
M.P: 120–123 ꢁC I.R: 1745.80 (–COO–), 1580 (–NO2),
1375 (–CF3). 1HNMR(CDCl3): d 1.28 (t, 3H, 30.215); 4.37
(q, 2H, J = 21.096); 5.21 (s, 2H); 8.02 (d, 1H, J = 9.065);
8.40 (d, 1H, J = 9.065)8.40 (s, 1H) Mass: 318 (M?, 20 %),
290 (90 %), 244(100 %). Anal. Calcd. for C12H10F3N3O4:
C, 45.43; H, 3.18; N, 13.25. Found: C, 45.42; H, 3.19; N,
13.26.
1-(4-Chlorobutyl)-6-nitro-2-trifluoromethyl-1H-
benzimidazole (4c)
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M.P: 70–74 ꢁC I.R: 1590 (–NO2), 1340 (–CF3). HNMR
(CDCl3): d 2.11–2.23 (m, 4H); 3.51 (t, 2H, J = 12.086);
4.45 (t, 2H, J = 15.108); 7.60 (d, 1H, J = 9.08); 8.34 (d,
1H, J = 9.08); 8.78 (s, 1H). Mass: 321 (M?, 35 %), 323
(12 %), 244 (65 %), 198 (30 %). Anal. Calcd. for
C12H11ClF3N3O2: C, 44.80; H, 3.45; N, 13.66. Found: C,
44.68; H, 3.44; N, 13.65.
Ethyl 2-(5-nitro-2-trifluoromethyl-1H-benzimidazole-
1-yl)acetate (4f)
M.P: 75–80 ꢁC I.R: 1737.54 (–COO–), 1585 (–NO2), 1370
(–CF3). HNMR(CDCl3): d 1.30 (t, 3H, 30.215); 4.31 (q,
2-(6-Nitro-2-trifluoromethyl-1H-benzimidazol-1-
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yl)acetonitrile (3d)
2H, J = 21.096); 5.10 (s, 2H); 7.48 (d, 1H, J = 9.065);
8.39 (d, 1H, J = 9.065); 8.80 (s, 1H) Mass: 318 (M?,
25 %), 290 (90 %), 244 (100 %). Anal. Calcd. for
C12H10F3N3O4: C, 45.43; H, 3.18; N, 13.25. Found: C,
45.41; H, 3.19; N, 13.26.
M.P: 145–150 ꢁC I.R: 2210.68 (–CN), 1340 (–CF3).
1HNMR(CDCl3): d 5.30 (s, 2H); 8.09 (d, 1H, J = 9.065);
8.40 (d, 1H, J = 9.065) 8.52 (s, 1H). Mass: 270 (M?,
100 %), 240 (78 %), 69 (58 %). Anal. Calcd. for
C10H5F3N4O2: C, 44.46; H, 1.87; N, 20.74. Found: C,
44.44; H, 1.86; N, 20.75.
1-(4-Chlorobutyl)-6-nitro-2-(perfluoroethyl)-1H-
benzimidazole (3g)
2-(5-Nitro-2-trifluoromethyl-1H-benz]imidazole-1-
M.P: 85–89 ꢁC I.R: 1580 (–NO2), 1385 (–CF3).
1HNMR(CDCl3): d 1.94–2.07 (m, 4H); 3.58 (t, 2H,
J = 12.086); 4.49 (t, 2H, J = 15.108); 7.92 (d, 1H,
J = 9.065); 8.25 (d, 1H, J = 9.065); 8.40 (s, 1H). Mass:
372 (M?, 100 %), 374 (33 %). Anal. Calcd. for
C13H11ClF5N3O2: C, 42.01; H, 2.98; N, 11.31. Found: C,
42.02; H, 2.98; N, 11.30.
yl)acetonitrile (4d)
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M.P: 93–95 ꢁC I.R: 2210 (–CN), 1345 (–CF3). HNMR
(CDCl3): d 5.30 (s, 2H); 7.71 (d, 1H, J = 9.357); 8.50 (d,
1H, J = 9.357) 8.90 (s, 1H). Mass: 270 (M?, 40 %), 240
(50 %), 69 (100 %). Anal. Calcd. for C10H5F3N4O2: C,
44.46; H, 1.87; N, 20.74. Found: C, 44.43; H, 1.85; N,
20.75.
1-(4-Chlrobutyl)-5-nitro-2-(perfluoroethyl)-1H-
benzimidazole (4g)
6-Nitro-1-(prop-2ynyl)-2-trifluoromethyl)-1H-
benzimidazole (3e)
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M.P: 80–82 ꢁC I.R: 1590 (–NO2), 1380 (–CF3). HNMR
(CDCl3): d 2.00–2.10 (m, 4H); 3.61 (t, 2H, J = 12.086);
4.52 (t, 2H, J = 15.108); 7.60 (d, 1H, J = 9.065); 8.31 (d,
1H, J = 9.065); 8.80 (s, 1H). Mass: 372 (M?, 100 %), 374
(33 %). Anal. Calcd. for C13H11ClF5N3O2: C, 42.01; H,
2.98; N, 11.31. Found: C, 42.02; H, 2.99; N, 11.30.
M.P: 120–125 ꢁC I.R: 2100 (–C:C–), 1580 (–NO2), 1345
(–CF3). HNMR(CDCl3): d 0.89 (t, 1H, 8.309); 5.89 (d,
2H, J = 6.798); 7.98 (d, 1H, J = 9.065); 8.30 (d, 1H,
J = 9.065); 8.71 (s, 1H). Mass: 270 (M?, 100 %). Anal.
Calcd. for C11H6F3N3O2: C, 49.08; H, 2.26; N, 15.02.
Found: C, 49.06; H, 2.25; N, 15.01.
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Ethyl-2-(6-nitro-2-(perfluoroethyl)-1H-benzimidazole-
1-yl)acetate (3h)
5-Nitro-1-(prop-2-ynyl)-2-trifluoromethyl-1H-
benzimidazole (4e)
M.P: 124–126 ꢁC I.R: 1754.45 (–COO–), 1590 (–NO2),
1385 (–CF3). 1HNMR(CDCl3): d 1.40 (t, 3H, J = 30.215);
4.31(q, 2H, J = 21.906); 5.20 (s, 2H); 8.09 (d, 1H,
J = 9.065); 8.41 (d, 1H, J = 9.065); 8.41 (s, 1H). Mass:
368 (M?, 100 %). Anal. Calcd. for C13H10F5N3O4: C,
42.52; H, 2.74; N, 11.44. Found: C, 42.51; H, 2.74; N,
11.45.
M.P: 75–80 ꢁC I.R: 2100 (–C:C–), 1580 (–NO2), 1345
(–CF3). HNMR(CDCl3): d 0.83 (t, 1H, 7.554); 5.75 (d,
2H, J = 6.798); 7.78 (d, 1H, J = 9.065); 8.30 (d, 1H,
J = 9.065); 8.72 (s, 1H). Mass: 270 (M?, 100 %). Anal.
Calcd. for C11H6F3N3O2: C, 49.08; H, 2.25; N, 15.01.
Found: C, 49.06; H, 2.26; N, 15.02.
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