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123.57, 127.58, 127.87, 129.00, 129.25, 129.31, 129.72, 130.27, hydrazone, H-2, H-6), 7.71–7.73 (t, 1H, J ¼ 8.00 Hz, phenyl
130.49, 130.66, 134.42, 135.56, 137.36, 141.99, 142.92, 145.14, hydrazone, H-3, H-4, H-5), 8.01–8.03 (d, 4H, J ¼ 8.00 Hz, phenyl
152.51, 167.39. Anal. calcd for C23H20N4O3S: C, 63.87; H, 4.66; N, H-2, H-6), 8.05–8.07 (d, 4H, J ¼ 8.00 Hz, phenyl H-3, H-5), 8.13 (s,
12.95; found: C, 64.13; H, 4.53; N, 13.24.
4.1.5.2 (E)-N0-(4-Chlorobenzylidene)-2-(2-(4-(methylsulfonyl)
1H CH]N), 11.82(s, 1H, NH, D2O exchangeable) 13C NMR (100
MHz DMSO-d6): d 43.72 (CH2 aliphatic), 46.27 (SO2CH3), 111.77,
phenyl)-1H-benzo[d]imidazol-1-yl) acetohydrazide (11b). Buff 112.91, 119.22, 121.15, 127.57, 127.86, 129.22, 130.30, 130.36,
solid; yield 56%; mp 148–150 ꢁC; IR: (KBr, cmꢀ1) 3407 (NH), 130.58, 130.61, 134.21, 135.18, 136.11, 138.19, 141.57, 142.35,
1698 (C]O), 1612 (C]N), 1316–1154 (SO2); 1HNMR (DMSO-d6, 143.73, 145.21, 153.50, 168.41, anal. calcd for C23H19ClN4O3S: C,
400 MHz, d ppm): 3.31 (s, 3H, SO2CH3), 5.62 (s, 2H, CH2), 7.31– 59.16; H, 4.10; N, 12.00; found: C, 59.42; H, 4.23; N, 11.79.
7.33 (t, 2H, J ¼ 8.00 Hz, benzimidazole H-5, H-6), 7.5–7.52 (d,
4.1.5.6 (E)-N0-(4-Chlorobenzylidene)-2-(5-chloro-2-(4-
2H, J ¼ 8.00 Hz, benzimidazole H-4, H-7), 7.77–7.79 (d, 4H, J ¼ (methylsulfonyl) phenyl)-1H-benzo[d]imidazol-1-yl) acetohydrazide
8.00 Hz, phenyl hydrazone H-2, H-3, H-5, H-6), 8.03–8.05 (d, 2H, (11f). Buff solid; yield 48%; mp 152–154 ꢁC; IR: (KBr, cmꢀ1) 3409
J ¼ 8.00 Hz, phenyl H-2, H-6), 8.09–8.10 (d, 2H, J ¼ 8.00 Hz, (NH), 1698 (C]O), 1616 (C]N), 1315, 1151 (SO2); 1HNMR
phenyl H-3, H-5), 8.12 (s, 1H, CH]N), 11.88 (s, 1H, NH, D2O (DMSO-d6, 400 MHz, d ppm): 3.31 (s, 3H, SO2CH3), 5.63 (s, 2H,
exchangble), Anal. calcd for C23H19ClN4O3S: C, 59.16; H, 4.10; N, CH2), 7.30–7.33 (m, 2H, benzimidazole, H-6, H-7), 7.50–7.52 (d,
12.00; found: C, 59.35; H, 4.22; N, 12.16.
2H, J ¼ 8.00 Hz, phenyl hydrazone, H-2, H-6), 7.77–7.79 (m, 3H,
4.1.5.3 (E)-N0-(4-Methoxybenzylidene)-2-(2-(4-(methylsulfonyl) benzimidazole, H4-phenyl hydrazone, H-3,H-5) 8.03–8.05 (d,
phenyl)-1H-benzo[d]imidazol-1-yl) acetohydrazide (11c). Off white; 2H, J ¼ 8.00 Hz, phenyl H-3, H-5), 8.09–8.11 (d, 4H, J ¼ 8.00 Hz,
yield 52%; mp 161–163 ꢁC; IR: (KBr, cmꢀ1) 3401 (NH), 1695 (C] phenyl H-2, H-6), 8.12 (s, 1H CH]N), 11.91 (s, 1H, NH, D2O
O), 1610, (C]N) 1311, 1150 (SO2); 1HNMR (DMSO-d6, 400 MHz, exchangeable), 13C NMR (100 MHz DMSO-d6): d 43.57 (CH2
d ppm): 3.31 (s, 3H, SO2CH3), 3.7 (s, 3H, OCH3), 5.58 (s, 2H, aliphatic), 46.20 (SO2CH3), 111.41, 119.26, 122.77, 123.76,
CH2), 6.94–6.98 (t, 2H, benzimidazole H-5, H-6), 7.3–7.32 (d, 2H, 127.89, 129.25, 129.33, 130.25, 133.27, 133.30, 136.06, 136.25,
J ¼ 8.00 Hz, benzimidazole H-4, H-7), 7.51–7.53 (d, 1H, J ¼ 136.26, 136.52, 136.94, 137.30, 142.03, 142.89, 143.86, 152.48,
8.00 Hz, phenyl hydrazone H-3), 7.61–7.63 (d, 2H, J ¼ 8.00 Hz, 164.12. Anal. calcd for C23H18Cl2N4O3S: C, 55.10; H, 3.62; N,
phenyl hydrazone H-2, H-6), 7.73–7.75 (d, 1H, J ¼ 8.00 Hz, 11.17; found: C, 55.37; H, 3.81; N, 11.43.
phenyl hydrazone H-5), 7.96–7.99 (d, 2H, J ¼ 8.00 Hz, phenyl H-
4.1.5.7 (E)-N0-(4-Methoxybenzylidene)-2-(5-chloro-2-(4-
2, H-6), 8.05–8.07 (d, 2H, J ¼ 8.00 Hz, phenyl H-3, H-5), 8.08 (s, (methylsulfonyl) phenyl)-1H-benzo[d]imidazol-1-yl) acetohydrazꢀid1e
1H CH]N), 11.6 (s, 1H, NH, D2O exchangeable), 13C DEPT-Q (11g). Yellow solid; yield 41%; mp 162–164 C; IR: (KBr, cm
)
ꢁ
NMR (100 MHz DMSO-d6): d 43.57 (CH2 aliphatic), 46.05, 3408 (NH), 1699 (C]O), 1615, (C]N), 1315–1152 (SO2); 1HNMR
(SO2CH3) 55.90, (OCH3), 111.43, 114.73, 114.86, 119.83, 122.96, (DMSO-d6, 400 MHz, d ppm): 3.31 (s, 3H, SO2CH3), 3.75 (s, 3H,
123.69, 124.60, 126.70, 127.89, 129.21, 129.36, 130.29, 130.60, OCH3), 5.51 (s, 2H, CH2), 6.92–6.94 (d, 2H, J ¼ 8.00 Hz benz-
135.49, 137.25, 141.99, 142.73, 146.10, 152.50, 161.32, 168.36. imidazole, H-6, H-7), 7.28–7.30 (d, 2H, J ¼ 8.00 Hz, phenyl
Anal. calcd for C24H22N4O4S C, 62.32; H, 4.79; N, 12.11; found: hydrazone, H-2, H-6), 7.58–7.60 (d, 3H, J ¼ 8.00 Hz, benzimid-
C, 62.60; H, 4.65; N, 12.37.
azole, H4-phenyl hydrazone, H-3, H-5), 7.94–7.96 (d, 2H, J ¼
8.00 Hz, phenyl H-2, H-6), 8.00–8.02 (d, 4H, J ¼ 8.00 Hz, phenyl
4.1.5.4 (E)-N0-(4-Fluorobenzylidene)-2-(2-(4-(methylsulfonyl)
phenyl)-1H-benzo[d]imidazol-1-yl) acetohydrazide (11d). Dark H-3, H-5), 8.06 (s, 1H CH]N)11.7 (s, 1H, NH, D2O exchangble),
yellow; yield 49%; mp 149–151 C; IR: (KBr, cmꢀ1) 3408 (NH), 13CNMR (100 MHz DMSO-d6): d 43.74 (CH2 aliphatic), 46.52
ꢁ
1699 (C]O), 1615 (C]N), 1313–1155 (SO2); 1HNMR (DMSO-d6, (SO2CH3), 55.77, 111.77, 114.72, 114.81, 119.24, 121.13, 123.27,
400 MHz, d ppm): 3.29 (s, 3H, SO2CH3), 5.62 (s, 2H, CH2), 7.27– 123.74, 126.85, 126.89, 127.37, 127.82, 129.34, 130.29, 130.69,
7.29 (t, 2H, benzimidazole H-5, H-6), 7.30–7.32 (d, 2H, J ¼ 130.72, 135.10, 138.18, 141.63, 142.24, 161.32, 168.18. Anal.
8.00 Hz, benzimidazole H-4, H-7), 7.77–7.82 (M, 4H, phenyl calcd for C24H21ClN4O4S: C, 58.00; H, 4.26; N, 11.27; found: C,
hydrazone, H-2, H-3, H-5, H-6) 8.04–8.06 (d, 2H, J ¼ 8.00 Hz, 57.78; H, 4.35; N, 11.51.
phenyl H-2, H-6), 8.10–8.12 (d, 2H, J ¼ 8.00 Hz, phenyl H-3, H-5),
4.1.5.8 (E)-N0-(4-Fluorobenzylidene)-2-(5-chloro-2-(4-
8.13 (s, 1H, CH]N), 11.84 (s, 1H, NH, D2O exchangeable). 13C (methylsulfonyl) phenyl)-1H-benzo[d]imidazol-1-yl) acetohydrazꢀid1e
ꢁ
NMR (100 MHz DMSO-d6): d 43.71 (CH2 aliphatic), 46.26 (11h). Pale yellow; yield 51%; mp 153–155 C; IR: (KBr, cm
)
(SO2CH3), 111.44, 116.20, 116.33, 119.74, 122.84, 123.62, 127.87, 3410 (NH), 1699 (C]O), 1618 (C]N), 1317–1153 (SO2); 1HNMR
129.75, 129.84, 130.26, 130.57, 130.98, 135.47, 137.29, 142.15, (DMSO-d6, 400 MHz, d ppm): 3.31 (s, 3H, SO2CH3), 5.65 (s, 2H,
142.92, 143.07, 143.85, 152.46, 162.38, 168.67, anal. calcd for CH2), 7.27–7.31 (m, 3H, benzimidazole H-4, H-6, H-7), 7.76–7.86
C
23H19FN4O3S: C, 61.32; H, 4.25; N, 12.44; found: C, 61.47; H, (m, 4H, J ¼ 8.4 Hz, phenyl hydrazone, H-2, H-3, H-5, H-6) 8.03–
4.18; N, 12.70.
8.05 (d, 2H, J ¼ 8.00 Hz, phenyl H-2, H-6), 8.08–8.10 (d, 4H, J ¼
8.00 Hz, phenyl H-3, H-5) 8.12 (s, 1H CH]N), 11.81 (s, 1H, NH,
4.1.5.5 (E)-N0-Benzylidene-2-(5-chloro-2-(4-(methylsulfonyl)
phenyl)-1H-benzo[d]imidazol-1-yl) acetohydrazide (11e). Pale D2O exchangeable), 13C NMR (100 MHz DMSO-d6): d 43.33 (CH2
brown solid; yield 45%; mp 149–151 C; IR: (KBr, cmꢀ1) 3404 aliphatic), 46.54 (SO2CH3), 111.75, 116.18, 116.39, 119.25,
ꢁ
(NH), 1695 (C]O), 1611 (C]N), 1312–1149 (SO2); 1HNMR 121.14, 123.29, 124.57, 127.92, 129.74, 129.83, 130.28, 130.32,
(DMSO-d6, 400 MHz, d ppm): 3.31 (s, 3H, SO2CH3), 5.64 (s, 2H, 130.93, 136.09, 141.63, 141.68, 142.25, 143.68, 143.93, 162.14,
CH2), 7.32–7.34 (d, 1H, J ¼ 8.00 Hz, benzimidazole, H-6), 7.44– 168.49, Anal. calcd for C23H18ClFN4O3S: C, 56.97; H, 3.74; N,
7.46 (d, 4H, J ¼ 8.00 Hz, benzimidazole H-4, H-7 phenyl 11.55; found: C, 57.12; H, 3.88; N, 11.69.
27668 | RSC Adv., 2021, 11, 27659–27673
© 2021 The Author(s). Published by the Royal Society of Chemistry