Med Chem Res
7.27–7.44 (m, 8H, Ar), 7.45–7.56 (m, 4H, Ar). 13C NMR
(CDCl3) d: 38.61 (CH2), 55.26 (OCH3), 113.69 (C3,5-Ar4),
127.10 (C1-Ar4), 127.68 (C4-Benzyl), 128.07 (C4-Ar5),
Ar5), 132.0 (C5-thiazole), 134.30 (C4-Ar5), 149.30 (C4-
thiazole), 157.20 (C4-Ar4), 162.77 (C2-thiazole). EI-Mass
m/z (%); 349 (33), 347 (100), 316 (20), 314 (60), 276 (22),
274 (66), 261 (60), 231 (18), 195 (26), 152 (28). Anal.
Calcd. For C17H14ClNOS2: C, 58.69; H, 4.06; N, 4.03.
Found: C, 58.89; H, 3.97; N, 3.88.
128.68 (C2,6-Benzyl), 128.78 (C3,5-Ar5), 129.20 (C3,5
-
Benzyl), 129.55 (C2,6-Ar5), 130.27 (C2,6-Ar4), 131.55 (C1-
Ar5), 131.96 (C5-thiazole), 136.66 (C1-Benzyl), 149.49
(C4-thiazole), 159.29 (C4-Ar4), 161.57 (C2-thiazole). EI-
Mass m/z (%); 389 (100), 356 (70), 240 (91), 226 (70),
197(20), 165 (16), 121 (12), 91 (40). Anal. Calcd. For
C23H19NOS2: C, 70.92; H, 4.92; N, 3.60. Found: C, 71.05;
H, 4.91; N, 3.52.
4-(4-Methoxyphenyl)-5-(4-chlorophenyl)-2-(ethylthio)-thi-
azole (6h) Yield: 42 %. Mp: 74–75 °C, IR (KBr, cm-1) m
3011, 2970, 2841, 1603, 1528, 1470, 1449, 1416, 1170,
1
1085, 1038, 970, 865, 829. H NMR (CDCl3) d: 1.50 (t,
J = 7.50 Hz, 3H, CH3), 3.27 (q, J = 7.50 Hz, 2H, CH2),
3.82 (s, 3H, OCH3), 6.84 (d, J = 8.5 Hz, 2H, H3,5-Ar4),
7.25 (d, J = 8.0 Hz, 2H, H3,5-Ar5), 7.29 (d, J = 8.5 Hz,
2H, H2,6-Ar4), 7.45 (d, J = 8.0 Hz, 2H, H2,6-Ar5). 13C
NMR (CDCl3) d: 14.67 (CH3), 28.74 (CH2), 55.26 (OCH3),
113.77 (C3,5-Ar4), 126.73 (C1-Ar4), 129.01 (C3,5-Ar5),
129.55 (C5-thiazole), 130.26 (C2,6-Ar4), 130.54 (C1-Ar5),
130.73 (C2,6-Ar5), 133.91 (C4-Ar5), 149.20 (C4-thiazole),
159.41 (C4-Ar4), 162.96 (C2-thiazole). EI-Mass m/z (%);
363 (33), 361 (100), 330 (60), 328 (20), 261 (13), 259 (41),
231 (10), 195 (12), 152 (16). Anal. Calcd. For
C18H16ClNOS2: C, 59.74; H, 4.46; N, 3.87. Found: C,
59.89; H, 4.52; N, 3.78.
4-(4-Methylthiophenyl)-5-(phenyl)-2-(methylthio)-thiazole
(6e) Yield: 46 %. Mp: 89–90 °C, IR (KBr, cm-1) m 3073,
2917, 1595, 1491, 1432, 1327, 1031, 853, 816, 750. H
1
NMR (CDCl3) d: 2.48 (s, 3H, SCH3), 2.75 (s, 3H, SCH3),
7.16 (d, J = 8.9 Hz, 2H, H2,6-Ar4), 7.32-7.36 (m, 5H, Ar5),
7.47 (d, J = 8.9 Hz, 2H, H3,5-Ar4). 13C NMR (CDCl3) d:
15.53 (SCH3), 16.68 (SCH3), 125.96 (C3,5-Ar4), 128.19
(C4-Ar5), 128.85 (C3,5-Ar5), 129.30 (C2,6-Ar4), 129.53
(C2,6-Ar5), 131.13 (C1-Ar4), 131.78 (C1-Ar5), 131.78 (C5-
thiazole), 138.29 (C4-Ar4), 149.07 (C4-thiazole), 164.16
(C2-thiazole). EI-Mass m/z (%); 329 (100), 296 (25), 267
(22), 241 (23), 208 (24), 165(17), 121 (12), 77 (10). Anal.
Calcd. For C17H15NS3: C, 61.97; H, 4.59; N, 4.25. Found:
C, 62.15; H, 4.51; N, 4.18.
4-(4-Methoxyphenyl)-5-(4-chlorophenyl)-2-(benzylthio)-
thiazole (6i) Yield: 72 %. Mp: 94–95 °C, IR (KBr,
cm-1) m 2850, 2837, 1603, 1531, 1495, 1326, 1244, 1173,
4-(4-Methylthiophenyl)-5-(phenyl)-2-(benzylthio)-thiazole
(6f) Yield: 67 %. Mp: 92–93 °C, IR (KBr, cm-1) m 3028,
2914, 1593, 1492, 1473, 1399, 1321, 1244, 1116, 1085,
1
1086, 953, 830. H NMR (CDCl3) d: 3.83 (s, 3H, OCH3),
4.52 (s, 2H, CH2), 6.86 (d, J = 8.5 Hz, 2H, H3,5-Ar4),
7.21–7.39 (m, 7H, Ar), 7.43–7.50 (m, 4H, Ar). 13C NMR
(CDCl3) d: 38.54 (CH2), 55.28 (OCH3), 113.82 (C3,5-Ar4),
126.70 (C1-Ar4), 127.71 (C4-Benzyl), 128.68 (C2,6-Ben-
1
1024, 958, 821, 751. H NMR (CDCl3) d: 2.49 (s, 3H,
SCH3), 4.52 (s, 2H, CH2), 7.16 (d, J = 7.0 Hz, 2H, H2,6
-
Ar4), 7.28–7.39 (m, 8H, Ar), 7.44–7.51 (m, 4H, Ar). 13C
NMR (CDCl3) d: 15.53 (SCH3), 38.59 (CH2), 125.95 (C3,5
Ar4), 127.70 (C4-Benzyl), 128.27 (C4-Ar5), 128.69 (C2,6
-
-
zyl), 129.03 (C3,5-Ar5), 129.17 (C3,5-Benzyl), 130.27 (C2,6-
Ar4), 130.46 (C1-Ar5), 130.76 (C2,6-Ar5), 131.54 (C5-thia-
zole), 134.00 (C4-Ar5), 136.52 (C1-Benzyl), 149.83 (C4-
thiazole), 159.47 (C4-Ar4), 162.10 (C2-thiazole). EI-Mass
m/z (%); 423 (100), 390 (86), 341(26), 274 (95), 207 (71),
135(35), 91 (95), 77 (41), 65 (32). Anal. Calcd. For
C23H18ClNOS2: C, 65.16; H, 4.28; N, 3.30. Found: C,
65.35; H, 4.18; N, 3.12.
Benzyl), 128.84 (C3,5-Ar5), 129.17 (C3,5-Benzyl), 129.29
(C2,6-Ar4), 129.55 (C2,6-Ar5), 131.02 (C1-Ar4), 131.66 (C1-
Ar5), 132.50 (C5-thiazole), 136.54 (C1-Benzyl), 138.36
(C4-Ar4), 148.95 (C4-thiazole), 162.02 (C2-thiazole). EI-
Mass m/z (%); 357 (18), 341 (40), 267 (80), 234 (26), 207
(100), 165 (15), 135 (44), 91 (65), 77 (42). Anal. Calcd. For
C23H19NS3: C, 68.11; H, 4.72; N, 3.45. Found: C, 68.25; H,
4.81; N, 3.38.
4-(4-Methylthiophenyl)-5-(4-chlorophenyl)-2-(benzylthio)-
thiazole (6j) Yield: 92 %. Mp: 112–113 °C, IR (KBr,
cm-1) m 3080, 3031, 2952, 1592, 1496, 1469, 1423, 1399,
4-(4-Methoxyphenyl)-5-(4-chlorophenyl)-2-(methylthio)-
thiazole (6g) Yield: 78 %. Mp: 95–96 °C, IR (KBr,
cm-1) m 3007, 2967, 2831, 1605, 1531, 1472, 1425, 1410,
1173, 1091, 1030, 960, 866, 821. 1H NMR (CDCl3) d: 2.74
(s, 3H, SCH3), 3.81 (s, 3H, OCH3), 6.84 (d, J = 8.5 Hz,
2H, H3,5-Ar4), 7.22–7.34 (m, 4H, Ar), 7.45 (d, J = 8.0 Hz,
2H, H2,6-Ar5). 13C NMR (CDCl3) d: 15.48 (SCH3), 54.20
1
1187, 1120, 1087, 863, 700. H NMR (CDCl3) d: 2.50 (s,
3H, SCH3), 4.51 (s, 2H, CH2), 7.18 (d, J = 8.5 Hz, 2H,
H
2,6-Ar4), 7.22–7.38 (m, 7H, Ar), 7.42–7.48 (m, 4H, Ar).
13C NMR (CDCl3) d: 15.48 (SCH3), 38.63 (CH2), 125.97
(C3,5-Ar4), 127.76 (C4-Benzyl), 128.70 (C2,6-Benzyl),
129.13 (C3,5-Ar5), 129.17 (C3,5-Benzyl), 129.29 (C2,6-Ar4),
130.12 (C1-Ar4), 130.48 (C1-Ar5), 130.75 (C2,6-Ar5),
131.90 (C5-thiazole), 134.30 (C4-Ar5), 136.39 (C1-Benzyl),
(OCH3), 114.1 (C3,5-Ar4), 125.97 (C1-Ar4), 129.13 (C3,5
-
Ar5), 130.12 (C2,6-Ar4), 130.48 (C1-Ar5), 130.75 (C2,6
-
123