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Med Chem Res (2013) 22:1925–1937
4-(5-Chloro-2-sulfonamido-thien-3-yl)-2-[(2-methylphen-
oxymethyl)phenyl]-[1,3]-thiazole (4e) IR (KBr, cmax
cm-1): 3384, 3112 (NH2), 3074 (ArC–H), 2980 (C–H), 1698
(C=N), 1599 (C=C), 1198 (C–O), 1078 (C–S), 768 (C–Cl);
1H NMR (CDCl3, 400 MHz) d: 2.17 (s, 3H, ring A-CH3),
5.25 (s, 2H, OCH2), 6.31 (s, 2H, –SO2NH2), 6.86–6.95 (m,
4H, rings A–H), 7.10–7.16 (m, 2H, rings B–H), 7.22 (s, 1H,
thiazole moiety), 7.27 (s, 1H, thioneyl moiety), 7.48–7.63
(m, 2H, rings B–H); LCMS: m/z 478 (M?, 100 %), 480
(M?2, 34 %).
B–H, J = 8.4 Hz), 7.84 (d, 1H, rings B–H, J = 8.4 Hz),
9.71 (s, 1H, NH2), 10.14 (s, 1H, NH2).
General procedure for the synthesis of 4-substituted-
2-[2-(aryloxymethyl)phenyl]-[1,3]-thiazoles (4a–p)
An equimolar mixture of the appropriate thioamide (3)
(0.01 mol) and phenacylbromide (0.01 mol) in ethanol
(10 mL) was refluxed for 4 h. After completion of the
reaction checked by TLC, the mixture was cooled to room
temperature and the solid obtained was filtered. The crude
product was recrystallized from ethanol. The character-
ization data of 4a–p are given in Table 1.
4-(5-Chloro-2-sulfonamido-thien-3-yl)-2-[(4-methylphen-
oxymethyl)phenyl]-[1,3]-thiazole (4g) IR (KBr, cmax
cm-1): 3394, 3125 (NH2), 3077 (ArC–H), 2989 (C–H),
1684 (C=N), 1592 (C=C), 1203 (C–O), 1065 (C–S), 766
1
(C–Cl); H NMR (CDCl3, 300 MHz) d: 2.23 (s, 3H, ring
4-(3-Carboxamido-2-hydroxy-phenyl)-2-[(2-methylphen-
oxymethyl)phenyl]-[1,3]-thiazole (4a) IR (KBr, m cm-1):
3428, 3128 (NH2), 3078 (ArC–H), 2950 (C–H), 1654
A-CH3), 5.33 (s, 2H, OCH2), 6.37 (s, 2H, –SO2NH2),
6.73–6.82 (m, 4H, rings A–H), 7.02 (s, 1H, thiazole moi-
ety), 7.12 (s, 1H, thioneyl moiety), 7.23–7.36 (m, 2H, rings
B–H), 7.38–7.52 (m, 2H, rings B–H); LCMS: m/z 478 (M?,
100 %), 480 (M?2, 33 %).
1
(C=N), 1599 (C=C), 1185 (C–O), 1080 (C–S); H NMR
(CDCl3, 400 MHz) d: 2.92 (s, 3H, ring A-CH3), 5.61 (s,
2H, OCH2), 6.82–6.97 (m, 4H, rings A–H), 7.11 (br.s, 2H,
–NH2), 7.46 (t, 2H, rings B–H, J = 8.4 Hz), 7.66 (br.s, 1H,
rings C–H), 7.78 (d, 2H, rings C–H, J = 8.8 Hz), 7.93 (d,
1H, rings B–H, J = 8.8 Hz), 7.97 (d, 1H, rings B–H,
J = 8.8 Hz), 8.39 (s, 1H, thiazole moiety), 12.76 (s, 1 H,
OH rings C); LCMS: m/z 416 (M?, 100 %).
4-(5-Chloro-2-sulfonamido-thien-3-yl)-2-[(4-chlorophen-
oxymethyl)phenyl]-[1,3]-thiazole (4h) IR (KBr, cmax
cm-1): 3387, 3120 (NH2), 3080 (ArC–H), 2985 (C–H),
1681(C=N), 1591 (C=C), 1188 (C–O), 1066 (C–S), 774
(C–Cl); 1H NMR (CDCl3, 300 MHz) d: 5.62 (s, 2H, OCH2),
6.32 (s, 2H, –SO2NH2), 6.60 (d, 2H, rings A–H, J = 8.8 Hz),
6.68 (d, 2H, rings A–H, J = 8.8 Hz), 6.74 (s, 1H, thiazole
moiety), 7.06 (s, 1H, thioneyl moiety), 7.12–7.27 (m, 2H,
rings B–H), 7.32–7.44 (m, 2H, rings B–H); LCMS: m/z 498
(M?, 100 %).
4-(3-Carboxamido-2-hydroxy-phenyl)-2-[(4-methylphen-
oxymethyl)phenyl]-[1,3]-thiazole (4c) IR (KBr, m cm-1):
3420, 3124 (NH2), 3081 (ArC–H), 2980 (C–H), 1689 (C=N),
1
1598 (C=C), 1195 (C–O), 1126 (C–S); H NMR (CDCl3,
400 MHz) d: 2.86 (s, 3H, ring A-CH3), 5.56 (s, 2H, OCH2),
6.76 (d, 2H, rings A–H, J = 8.4 Hz), 6.88 (d, 2H, rings A–H,
J = 8.4 Hz), 7.05 (br.s, 2H, –NH2), 7.40 (t, 2H, rings B–H,
J = 7.8 Hz), 7.57–7.66 (m, 2H, rings B–H), 7.71 (br.s, 1H,
rings C–H), 7.82 (d, 2H, rings C–H, J = 8.8 Hz), 8.21 (s, 1H,
thiazole moiety), 12.67 (s, 1H, OH ring C).
4-(3-Bromophenyl)-2-[(2-methylphenoxymethyl)phenyl]-
[1,3]-thiazole (4i) IR (KBr, cmax cm-1): 3082 (ArC–H),
2990 (C–H), 1684 (C=N), 1596 (C=C), 1185 (C–O), 1065
(C–S), 585 (C–Br); 1H NMR (CDCl3, 300 MHz) d: 2.90 (s,
3H, ArCH3), 5.67 (s, 2H, OCH2), 6.86–7.16 (m, 4H, rings
A–H), 7.19 (s, 1H, rings C–H), 7.30–7.44 (m, 3H, rings
C–H), 7.52 (d, 1H, rings B–H, J = 8.2 Hz), 7.61 (t, 2H,
rings B–H, J = 7.8 Hz), 7.73 (d, 1H, rings B–H,
J = 8.4 Hz), 7.82 (s, 1H, thiazole moiety).
4-(3-Carboxamido-2-hydroxy-phenyl)-2-[(4-chlorophen-
oxymethyl)phenyl]-[1,3]-thiazole (4d) IR (KBr, m cm-1):
3428, 3128 (NH2), 3086 (ArC–H), 2970 (C–H), 1686
(C=N), 1590 (C=C), 1205 (C–O), 1088 (C–S), 784 (C–Cl);
1H NMR (CDCl3, 400 MHz) d: 5.45 (s, 2H, OCH2), 6.86
(d, 2H, rings A–H, J = 8.8 Hz), 7.20 (d, 2H, rings A–H,
J = 8.8 Hz), 7.31 (br.s, 2H, –NH2), 7.46 (t, 2H, rings B–H,
J = 8.1 Hz), 7.72 (br.s, 1H, rings C–H), 7.83 (d, 2H, rings
C–H, J = 8.4 Hz), 7.99 (d, 1H, rings B–H, J = 8.4 Hz),
8.18 (d, 1H, rings B–H, J = 8.4 Hz), 8.42 (s, 1H, thiazole
moiety), 12.58 (s, 1 H, OH of ring C); LCMS: m/z 438
(M?, 100 %), 440 (M?2, 33 %).
4-(4-Nitrophenyl)-2-[(2-methylphenoxymethyl)phenyl]-
[1,3]-thiazole (4m) IR (KBr, cmax cm-1): 3084 (ArC–H),
2960 (C–H), 1675 (C=N), 1594 (C=C), 1450 (NO2), 1200
(C–O), 1170 (NO2), 1078 (C–S); 1H NMR (CDCl3,
400 MHz) d: 2.32 (s, 3H, ArCH3), 5.55 (s, 2H, OCH2),
6.78–6.84 (m, 3H, rings A–H), 7.18–7.26 (m, 1H, rings
A–H), 7.48 (t, 2H, rings B–H, J = 8.1 Hz), 7.73 (d, 1H,
rings B–H, J = 8.8 Hz), 7.78 (d, 1H, rings B–H,
J = 8.8 Hz), 7.85 (s, 1H, thiazole moiety), 8.02 (d, 2H,
123