ALP et al./Turk J Chem
2-((2-(4-Chlorophenyl)-1H -benzo[d]imidazol-1-yl)methyl)-5-(4-fluorobenzylthio)-1,3,4-oxadiazole
(8)
Crude 8 was recrystallized from ethanol to provide 8 (yield 38%) as a white solid, mp 127–128 ◦ C. MS (ESI+)
M+H (%): 451 (100), 453 (47). 1 H NMR δ ppm (CDCl3): 7.83–7.86 (m, 1H), 7.79 (d, 2H, J = 8.8 Hz), 7.55
(d, 2H, J = 8.8 Hz), 7.50–7.52 (m, 1H), 7.30–7.39 (m, 4H), 6.96 (t, 2H, J = 8.8 Hz), 5.51 (s, 2H, –N–CH2),
4.40 (s, 2H, –S–CH2). 13 C NMR δ ppm (CDCl3): 165.7, 163.7, 162.3, 152.5, 142.9, 136.8, 135.4, 130.9, 130.8,
129.4, 127.6, 123.9, 123.5, 120.4, 115.9, 115.7, 110.1, 39.6, 36.1.
2-((2-(4-Chlorophenyl)-1H -benzo[d]imidazol-1-yl)methyl)-5-(4-nitrobenzylthio)-1,3,4-oxadiazole
(9)
Crude 9 was recrystallized from ethanol to provide 9 (yield 40%) as a white solid, mp 154–155 ◦ C. MS (ESI+)
M+H (%): 478 (100), 480 (43). 1 H NMR δ ppm (CDCl3): 8.12 (d, 2H, J = 9.2 Hz), 7.82–7.85 (m, 1H), 7.78
(d, 2H, J = 8.4 Hz), 7.54 (d, 4H, J = 8.8 Hz), 7.47–7.50 (m, 1H), 7.33–7.37 (m, 2H), 5.51 (s, 2H, –N–CH2),
4.47 (s, 2H, –S–CH2). 13 C NMR δ ppm (CDCl3): 164.9, 162.6, 152.5, 147.6, 142.9, 142.8, 136.8, 135.4, 130.9,
129.9, 129.4, 127.6, 123.9, 123.6, 120.4, 109.9, 39.5, 35.6.
2-((2-(4-(Benzyloxy)phenyl)-1H -benzo[d]imidazol-1-yl)methyl)-5-(4-bromobenzylthio)-1,3,4-
oxadiazole (10)
Crude 10 was recrystallized from ethanol to provide 10 (yield 53%) as a white solid, mp 119–121 ◦ C. MS
(ESI+) M+H (%): 583 (100), 585 (97). 1 H NMR δ ppm (CDCl3): 7.82 (d, 1H, J = 7.2 Hz), 7.76 (d, 2H, J
= 8.0 Hz), 7.31–7.46 (m, 10H), 7.20 (d, 2H, J = 7.6 Hz), 7.14 (d, 2H, J = 8.4 Hz), 5.51 (s, 2H, –O–CH2), 5.15
(s, 2H, –N–CH2), 4.34 (s, 2H, –S–CH2). 13 C NMR δ ppm (CDCl3): 165.6, 162.9, 160.6, 153.9, 143.2, 136.6,
135.6, 134.5, 132.2, 131.3, 130.9, 128.9, 128.4, 127.7, 123.7, 123.5, 122.5, 121.8, 120.3, 115.7, 110.2, 70.4, 39.9,
36.3.
2-((2-(4-(Benzyloxy)phenyl)-1H -benzo[d]imidazol-1-yl)methyl)-5-(2,4-dichlorobenzylthio)-1,3,4-
oxadiazole (11)
Crude 11 was purified by column chromatography (n-hexane/ethyl acetate (2:1)) to provide 11 (yield 36%) as
a white solid, mp 124–125 ◦ C. MS (ESI+) M+H (%): 573 (100), 575 (91), 577 (20). 1 H NMR δ ppm (CDCl3):
7.81 (d, 1H, J = 6.8 Hz), 7.76 (d, 2H, J = 8.8 Hz), 7.28–7.48 (m, 10H), 7.14 (d, 2H, J = 9.2 Hz), 7.11 (dd,
1H, J = 8.0 Hz, J = 2.0 Hz), 5.51 (s, 2H, –O–CH2), 5.15 (s, 2H, –N–CH2), 4.46 (s, 2H, –S–CH2). 13 C NMR
δ ppm (CDCl3): 165.5, 162.8, 160.4, 153.7, 142.9, 136.4, 135.4, 134.9, 134.9, 132.2, 131.9, 131.1, 129.6, 128.7,
128.2, 127.5, 127.4, 123.4, 123.3, 121.6, 120.1, 115.4, 109.9, 70.1, 39.6, 33.9.
2-((2-(4-(Benzyloxy)phenyl)-1H -benzo[d]imidazol-1-yl)methyl)-5-(4-nitrobenzylthio)-1,3,4-oxa-
diazole (12)
Crude 12 was purified by column chromatography (n-hexane/ethyl acetate (2:1)) to provide 12 (yield 37%) as
a yellowish solid, mp 69–71 ◦ C. MS (ESI+) M+H (%): 550 (100). 1 H NMR δ ppm (CDCl3): 8.11 (d, 2H, J
= 8.4 Hz), 7.82 (d, 1H, J = 7.2 Hz), 7.76 (d, 2H, J = 8.8 Hz), 7.52 (d, 2H, J = 8.4 Hz), 7.28–7.47 (m, 8H),
7.14 (d, 2H, J = 8.8 Hz), 5.52 (s, 2H, –O–CH2), 5.15 (s, 2H, –N–CH2), 4.45 (s, 2H, –S–CH2). 13 C NMR
49