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6.1.11. Synthesis of 6-chloro-2-({[(E)-2-(4-fluoro-3-
methyl phenyl)-1-ethenyl]sulfonyl}methyl)-1-(methyl
sulfonyl)-1H-benzo[d]imidazole (6e)
SO2Me); Mass (m/z) (DIP): 429 (Mꢃ), 391, 351
(100%), 287, 279, 254, 245, 231.
Yield (35%); m.p. 194Á
2932, 1607, 1501, 1368, 1302, 1234, 1168, 1125, 1048;
1H-NMR (CDCl3): dH 7.0 (m, 8H, Ar), 5.2 (s, 2H, Á
/
195 8C; IR (KBr) cmꢀ1: 3018,
6.1.17. Synthesis of4-{(E)-2-[(1H-benzo[d]imidazol-2-
yl methyl} sulfonyl]-1-ethenyl}-2,6-di{tert-butyl} phenol
(7a)
/
Yield (50%); m.p. 142Á
2963, 1713, 1674, 1616, 1548, 1439, 1362, 1310, 1225,
1201; 1H-NMR (CDCl3), dH 7.6 (m, 2H, Ar), 7Á
7.45 (m,
5H, Ar), 6.8 (d, 1H, Jꢂ15.6 Hz, styryl), 6.2 (s, 1H, OH),
/
144 8C; IR (KBr) cmꢀ1: 3610,
CH2), 3.8 (s, 3H, SO2Me), 2.2 (s, 3H,ÁCH3); Mass m/z
/
(DIP): 443 (Mꢃ), 365 (100%), 301, 245, 167.
/
/
6.1.12. Synthesis of 6-chloro-2-({[(E)-2-(4-
chlorophenyl)-1-ethenyl]sulfonyl}methyl)-1-
(methylsulfonyl)-1H-benzo[d]imidazole (6f)
4.6 (s, 2H, CH2), 1.4 (s, 18H, di-tert.butyl); Mass (m/z)
(DIP): 427 (, Mꢃ,100%), 362, 217, 132.
Yield (39%); m.p. 230Á
232 8C; IR (KBr) cmꢀ1: 3020,
2950, 1619, 1527, 1492, 1454, 1367, 1303, 1259, 1168,
/
6.1.18. Synthesis of 1-(1H-benzo[d]imidazol-2-yl
methyl[(E)-2-{4-methoxy phenyl}-1-ethenyl]sulfone
(7b)
1
1129, 1097; H-NMR (CDCl3): dH 7.2 (m, 9H, Ar), 7.0
(d, 1H, styryl, Jꢂ
3H, Á
SO2Me); Mass (m/z) (DIP): 406 (Mꢃ, 100%), 367,
303.
/
15.6 Hz), 5.2 (s,2H, Á/CH2), 3.8 (s,
Yield (53%); m.p. 190Á
191 8C; IR (KBr) cmꢀ1: 3060,
3002, 2940, 2835, 1599, 1511, 1433, 1404, 1308, 1291,
/
/
1
1257, 1173; H-NMR (CDCl3), dH 7.2 (m, 7H, Ar), 6.6
(m, 3H, Ar), 4.8 (s, 2H, CH2), 3.8 (s, 3H, OCH3); Mass
(m/z) (DIP): 329 (Mꢃ, 100%), 264, 249, 149, 132.
6.1.13. Synthesis of 2-({[(E)-2-(3,4-dichlorophenyl)-1-
ethenyl]sulfonyl}methyl)-1-(methylsulfonyl)-1H-
benzo[d]imidazole (6g)
Yield (44%); m.p. 194Á
2854, 1614, 1584, 1467, 1371, 1302, 1251, 1172, 1129;
1H-NMR (CDCl3), dH 7.0 (m, 9H, Ar), 5.2 (s, 2H, Á
/
196 8C; IR (KBr) cmꢀ1: 3026,
6.1.19. Synthesis of 1H-benzo[d]imidazol-2-yl
methyl[{E}-2-(4-bromophenyl)-1-ethenyl]sulfone (7c)
211 8C; IR (KBr) cmꢀ1: 3331,
/
Yield (49%); m.p. 209Á
3057, 1613.8, 1587, 1488, 1454, 1433, 1305;1H-NMR
(CDCl3), dH 7.2 (m, 9H, Ar), 6.8 (d, 1H, styryl, Jꢂ15.2
2), 381
/
CH2), 3.8(s, 3H, ÁSO2CH3); Mass (m/z) (DIP): 445
/
(Mꢃ), 367 (100%), 333, 303, 211.
/
Hz), 4.8 (s, 2H); Mass (m/z) (DIP): 379 (Mꢃꢃ
/
(Mꢃ), 315, 299, 183, 133, 113.
6.1.14. Synthesis of 2-({[(E)-2-(4-chlorophenyl)-1-
ethenyl]sulfonyl}methyl)-1-(methylsulfonyl)-1H-
benzo[d]imidazole (6h)
6.1.20. Synthesis of 1H-benzo[d]imidazol-2-yl
methyl[{E}-2-(4-fluoro-3-methyl phenyl)-1-
ethenyl]sulfone (7d)
Yield (45%); m.p. 189Á
1591, 1490, 1449, 1365, 1295, 1170, 1126, 1053, 1013;
1H-NMR (CDCl3), dH 7.7(dd, 2H, Jꢂ
9.2 Hz, Ar), 7.3
/
191 8C; IR (KBr) cmꢀ1: 3022,
79 8C; IR (KBr) cmꢀ1: 3282,
/
Yield (45%); m.p. 177Á
/
(m,7H, Ar), 7.0 (d,1H, Jꢂ
/
15.6 Hz, styryl), 5.2 (s, 2H, Á
/
3026, 2998, 1703, 1615, 1589, 1502, 1442, 1402, 1328,
CH2), 3.6 (s, 3H); Mass (m/z) (DIP): 411(Mꢃ), 333, 269,
211, 133, 104, 94.
1
1299, 1257, 1190, 1130; H-NMR (DMSO-d6ꢃ
dH 2.2 (s, 2H), 6.8 (d, 1H, Jꢂ8.4 Hz), 7.0 (t, 1H, Jꢂ
7.6 (m, 3H); Mass (m/z) (CI):
/
CDCl3),
/
/8
Hz), 7.1Á
/
7.4 (m, 4H), 7.4Á
/
330 (Mꢃ), 260, 132 (100%), 104, 91.
6.1.15. Synthesis of 2-({[(E)-2-(4-chloro-3-
methylphenyl)-1-ethenyl]sulfonyl}methyl)-1-
(methylsulfonyl)-1H-benzo[d]imidazole (6i)
6.1.21. Synthesis of 6-chloro-1H-benzo[d] imidazol-2-
yl)methyl[(E)-2-(4-fluoro-3-methyl phenyl)-1-
ethenyl]sulfone (7e)
Yield (45%); m.p. 204Á
206 8C; IR (KBr) cmꢀ1: 3423,
3058, 3022, 2939, 1620,1527, 1483, 1452, 1363, 1307,
/
1
1246, 1168; H-NMR (CDCl3), dH 7.7 (m, 2H, Ar), 7.2
Yield (37%); m.p. 111Á
/
113 8C; IR (KBr) cmꢀ1: 3421,
2928, 1604, 1501, 1431, 1311, 1256, 1147, 1110; 1H-
(m, 6H), 7.0 (d, 1H, Jꢂ15.2 Hz, styryl), 3.6 (s, 3H), 2.4
/
(s, 3H); Mass (m/z) (DIP): 425 (Mꢃ), 347, 283, 211, 195,
185, 165, 153, 133 (100%), 112.
NMR (CDCl3): 2.2 (s, 3H), 4.8 (s, 2H), 6.7Á7.8 (m, 8H);
/
Mass (m/z) (CI): 365 (Mꢃ), 300, 285, 165 (100%), 136,
109, 97.
6.1.16. Synthesis of 6-chloro-2-({[(E)-2-(4-
fluorophenyl)-1-ethenyl]sulfonyl}methyl)-1-
(methylsulfonyl)-1H-benzo[d]imidazole (6j)
6.1.22. Synthesis of 6-chloro-1H-benzo[d]imidazol-2-
yl)methyl[(E)-2-(4-chloro phenyl)-1-ethenyl sulfone
(7f)
Yield (44%); m.p. 196Á
98 8C; IR (KBr) cmꢀ1: 3443,
3020, 2928, 1601, 1510, 1455, 1367, 1302, 1238, 1167,
/
Yield (33%); m.p. 187Á
2928, 1616, 1591,1528, 1491, 1431, 1309, 1145; 1H-NMR
(CDCl3): 4.8 (s, 2H), 6.8 (d,1H, Jꢂ16 Hz), 7.2Á7.8 (m,
/
185 8C; IR (KBr) cmꢀ1: 3384,
1126; 1H-NMR (CDCl3) dH 7.1 (m, 8H, Ar), 7.0 (d, 1H,
styryl, Jꢂ
/
14.6Hz), 5.2 (s, 2H, Á/CH2), 3.6 (s, 3H,
/
/