6.83-6.89 (m, 1H, ArH), 7.10 (s, 1H, ArH), 7.19-7.27 (m, 4H,
ArH), 7.34 (d, J= 7.5, 1H, ArH), 7.57 (s, 2H, ArH), 7.87-7.90 (m,
1H, ArH), 8.17 (d, J= 9.5, 1H, ArH), 9.33 (bs, 1H, NH). Anal.
Calcd for C23H20BrN3O3S2: C: 52.08; H: 3.80; N: 7.92; Found: C:
52.25; H: 4.03; N: 8.08.
7.27 (m, 3H, ArH), 7.70 (d, J= 7.5, 1H, ArH), 8.17 (d, J= 8.5,
1H, ArH), 10.53 (bs, 1H, NH). Anal. Calcd for C25H24ClN3OS:
C: 66.73; H: 5.38; N: 9.34; Found: C: 66.92; H: 5.59; N: 9.60.
2-{[6-Chloro-1-(3,5-dimethylbenzyl)-1H-benzimidazol-2-
yl]sulfanyl}-N-2-chloro-4-methylphenylacetamide (5b).
2-({6-Chloro-1-[(3,5-dimethylphenyl)sulfonyl]-1H-
benzimidazol-2-yl}sulfanyl)-N-2-bromophenylacetamide (3d).
Mp: 164-166 °C, yield 80%, Rf: 0,40 (cyclohexane/EtOAc=
8:2). H NMR (CDCl3): 2.27 (s, 6H, CH3), 2.29 (s, 3H, CH3),
1
Mp: 182-184 °C, yield 75%, Rf: 0,46 (cyclohexane/EtOAc=
8:2). H NMR (CDCl3): 2.33 (s, 6H, CH3), 4.19 (s, 2H, CH2),
4.16 (s, 2H, CH2), 5.17 (s, 2H, CH2), 6.77 (s, 2H, ArH), 6.95 (s,
1H, ArH), 7.06 (d, J= 8.2, 1H, ArH), 7.13 (s, 1H, ArH), 7.22-
7.28 (m, 3H, ArH), 7.61 (d, J= 7.7, 1H, ArH), 8.19 (d, J= 8.7,
1H, ArH), 10.36 (bs, 1H, NH). Anal. Calcd for C25H23Cl2N3OS:
C: 61.98; H: 4.79; N: 8.67; Found: C: 62.32; H: 5.01; N: 8.80.
1
6.96 (t, J= 7.7, 1H, ArH), 7.22-7.33 (m, 3H, ArH), 7.44 (d, J=
9.4, 1H, ArH), 7.55 (d, J= 8.9, 1H, ArH), 7.65 (s, 2H, ArH), 8.00
(s, 1H, ArH), 8.26 (d, J= 6.6, 1H, ArH), 9.26 (bs, 1H, NH). Anal.
Calcd for C23H19BrClN3O3S2: C: 48.90; H: 3.39; N: 7.44; Found:
C: 49.13; H: 3.53; N: 7.67.
2-({1-[(3,5-Dimethylphenyl)sulfonyl]-1H-benzimidazol-2-
yl}sulfanyl)-N-2-chloro-4-methylphenylacetamide (5c).
2-{[1-(3,5-Dimethylbenzyl)-1H-benzimidazol-2-
yl]sulfanyl}-N-2-nitrophenylacetamide (4a).
Mp: 167-169 °C, yield 46%, Rf: 0,30 (cyclohexane/EtOAc=
8:2). H NMR (CDCl3): 2.27 (s, 3H, CH3), 2.31 (s, 6H, CH3),
1
Mp: 152-152 °C, yield 98%, Rf: 0,34 (cyclohexane/EtOAc=
8:2). H NMR (CDCl3): 2.24 (s, 6H, CH3), 4.25 (s, 2H, CH2),
4.15 (s, 2H, CH2), 7.05 (d, J= 8.3, 2H, ArH), 7.18 (s, 1H, ArH),
7.33-7.36 (m, 2H, ArH), 7.61-7.65 (m, 3H, ArH), 7.97 (d, J= 6.6,
1H, ArH), 8.19 (d, J= 8.2, 1H, ArH), 9.62 (bs, 1H, NH). Anal.
Calcd for C24H22ClN3O3S2: C: 57.65; H: 4.43; N: 8.40; Found: C:
57.98; H: 4.71; N: 8.69
1
5.23 (s, 2H, CH2), 6.79 (s, 2H, ArH), 6.90 (s, 1H, ArH), 7.15-
7.25 (m, 4H, ArH), 7.59 (t, J= 8.5, 1H, ArH), 7.82 (d, J= 7.5, 1H,
ArH), 8.09 (d, J= 8.5, 1H, ArH), 8.57 (d, J= 8.5, 1H, ArH), 11.64
(bs, 1H, NH). Anal. Calcd for C24H22N4O3S: C: 64.56; H: 4.97;
N: 12.55; Found: C: 64.77; H: 5.08; N: 12.69.
2-({6-Chloro-1-[(3,5-dimethylphenyl)sulfonyl]-1H-
benzimidazol-2-yl}sulfanyl)-N-2-chloro-4-
methylphenylacetamide (5d).
2-{[6-Chloro-1-(3,5-dimethylbenzyl)-1H-benzimidazol-2-
yl]sulfanyl}-N-2-nitrophenylacetamide (4b).
Mp: 163-165 °C, yield 45%, Rf: 0,34 (cyclohexane/EtOAc=
8:2). H NMR (CDCl3): 2.28 (s, 3H, CH3), 2.33 (s, 6H, CH3),
1
Mp: 166-168 °C, yield 86%, Rf: 0,28 (cyclohexane/EtOAc=
1
8:2). H NMR (CDCl3): 2.28 (s, 6H, CH3), 4.26 (s, 2H, CH2),
4.13 (s, 2H, CH2), 7.05 (d, J= 8.7, 2H, ArH), 7.22 (s, 1H, ArH),
7.28-7.33 (m, 2H, ArH), 7.53 (d, J= 8.2, 1H, ArH), 7.65 (s, 2H,
ArH), 7.99 (s, 1H, ArH), 8.18 (d, J= 8.2, 1H, ArH), 9.48 (bs, 1H,
NH). Anal. Calcd for C24H21Cl2N3O3S2: C: 53.93; H: 3.96; N:
7.86; Found: C: 54.28; H: 4.09; N: 7.99.
5.21 (s, 2H, CH2), 6.79 (s, 2H, ArH), 6.95 (s, 1H, ArH), 7.18-
7.23 (m, 3H, ArH), 7.63 (t, J= 7.2, 1H, ArH), 7.74 (d, J= 9.2, 1H,
ArH), 8.13 (d, J= 8.7, 1H, ArH), 8.62 (d, J= 8.7, 1H, ArH), 1.57
(bs, 1H, NH). Anal. Calcd for C24H21ClN4O3S: C: 59.93; H: 4.40;
N: 11.65; Found: C: 64.77; H: 5.08; N: 12.69.
Methyl-3-chloro-4-[({[1-(3,5-dimethylphenyl)-1H-
2-({1-[(3,5-Dimethylphenyl)sulfonyl]-1H-benzimidazol-2-
benzimidazol-2-yl]sulfanyl}acetyl)amino] benzoate (6a).
yl}sulfanyl)-N-2-nitrophenylacetamide (4c).
Mp: 192-194 °C, yield 55%, Rf: 0,43 (cyclohexane/EtOAc=
8:2). H NMR (CDCl3): 2.24 (s, 6H, CH3), 3.89 (s, 3H, CH3),
1
Mp: 183-185 °C, yield 40%, Rf: 0,64 (cyclohexane/EtOAc=
1
6:4). H NMR (CDCl3): 2.33 (s, 6H, CH3), 4.20 (s, 2H, CH2),
4.19 (s, 2H, CH2), 5.20 (s, 2H, CH2), 6.79 (s, 2H, ArH), 6.91 (s,
1H, ArH), 7.23-7.26 (m, 3H, ArH), 7.70 (d, J= 7.4, 1H, ArH),
7.90 (d, J= 9.1, 1H, ArH), 7.99 (s, 1H, ArH), 8.50 (d, J= 8.5, 1H,
ArH), 9.48 (bs, 1H, NH). Anal. Calcd for C26H24ClN3O3S: C:
63.21; H: 4.90; N: 8.51; Found: C: 63.55; H: 5.26; N: 8.84.
5.23 (s, 2H, CH2), 7.16-7.30 (m, 5H, ArH), 7.61-7.89 (m, 4H,
ArH), 8.10 (d, J= 7.4, 1H, ArH), 8.61 (d, J= 7.4, 1H, ArH), 11.22
(bs, 1H, NH). Anal. Calcd for C23H20N4O5S2: C: 55.63; H: 4.06;
N: 11.28; Found: C: 56.79; H: 4.21; N: 11.49.
2-({6-Chloro-1-[(3,5-dimethylphenyl)sulfonyl]-1H-
Methyl-3-chloro-4-[({[6-chloro-1-(3,5-dimethylphenyl)-1H-
benzimidazol-2-yl}sulfanyl)-N-2-nitrophenylacetamide (4d).
benzimidazol-2-yl]sulfanyl}acetyl)amino] benzoate (6b).
Mp: 150-152 °C, yield 50%, Rf: 0,56 (cyclohexane/EtOAc=
6:4). H NMR (CDCl3): 2.37 (s, 6H, CH3), 4.20 (s, 2H, CH2),
Mp: 177-179 °C, yield 76%, Rf: 0,41 (cyclohexane/EtOAc=
8:2). H NMR (CDCl3): 2.27 (s, 6H, CH3), 3.91 (s, 3H, CH3),
1
1
7.20-7.31 (m, 3H, ArH), 7.65-7.69 (m, 3H, ArH), 7.94 (s, 1H,
ArH), 8.13 (d, J= 7.7, 1H, ArH), 8.64 (d, J= 8.9, 1H, ArH), 11.18
(bs, 1H, NH). Anal. Calcd for C23H19ClN4O5S2: C: 52.02; H:
3.61; N: 10.55; Found: C: 52.31; H: 3.86; N: 10.76.
4.19 (s, 2H, CH2), 5.17 (s, 2H, CH2), 6.77 (s, 2H, ArH), 6.95 (s,
1H, ArH), 7.24-7.28 (m, 3H, ArH), 7.61 (d, J= 8.8, 1H, ArH),
7.93 (d, J= 8.8, 1H, ArH), 8.01 (s, 1H, ArH), 8.52 (d, J= 8.3, 1H,
ArH), 10.70 (bs, 1H, NH). Anal. Calcd for C26H23Cl2N3O3S: C:
59.09; H: 4.39; N: 7.95; Found: C: 59.23; H: 4.50; N: 8.12.
2-{[1-(3,5-Dimethylbenzyl)-1H-benzimidazol-2-
yl]sulfanyl}-N-2-chloro-4-methylphenylacetamide (5a).
Methyl-3-chloro-4-{[({1-[(3,5-dimethylphenyl)sulfonyl]-
1H-benzimidazol-2-yl}sulfanyl)acetyl]amino}benzoate (6c).
Mp: 123-125 °C, yield 57%, Rf: 0,42 (cyclohexane/EtOAc=
8:2). H NMR (CDCl3): 2.24 (s, 6H, CH3), 2.26 (s, 3H, CH3),
4.16 (s, 2H, CH2), 5.19 (s, 2H, CH2), 6.78 (s, 2H, ArH), 6.91 (s,
1
Mp: 187-189 °C, yield 56%, Rf: 0,41 (cyclohexane/EtOAc=
1
8:2). H NMR (CDCl3): 2.29 (s, 6H, CH3), 3.89 (s, 3H, CH3),
1H, ArH), 7.03 (d, J= 8.5, 1H, ArH), 7.11 (s, 1H, ArH), 7.19-
4.17 (s, 2H, CH2), 7.17 (s, 1H, ArH), 7.33-7.38 (m, 2H, ArH),