Med Chem Res
cyclohexene ring), 3.71 (s, 2H, –CH2 proton of thiazolid-
inone ring), 2.98 (m, 2H, –CH2 proton of fused cyclohex-
ene ring). 13CNMR-DEPT-135 (100 MHz, CDCl3): 29.59
(CH2 carbon of fused cyclohexene ring), 31.74 (CH2 car-
bon of thiazolidinone ring), 41.99 (CH carbon of fused
cyclohexene ring), 55.71 (OCH3 carbon of bromophenyl
ring), 60.14 (CH carbon of thiazolidinone ring), 114.98,
118.55, 125.79, 126.01, 127.52, 128.11, 129.87, 130.23,
130.45, 134.30. LCMS m/z: 639 (m ? 1, mol. wt. =
638.78, C27H20BrCl3N2O3S).
([C–Br), 732.1 (C–Cl). 1H-NMR: (CDCl3, d/ppm,
400 MHz), 10.72 (s, 1H, NH), 7.46–7.58 (m, 5H, ArH),
6.96–6.98 (m, 1H, ArH), 6.685–6.692 (m, 1H, ArH), 5.96
(s, 1H, CH, thiazolidinone ring), 3.78–4.0 (m, 2H, CH2,
thiazolidinone ring), 3.71 (s, 3H, OCH3). LCMS m/z: 443
(m ? 1, mol. wt. = 441.7, C17H14BrClN2O3S).
2-Bromo-N-[2-(2,4-dimethoxyphenyl)-4-oxo-1,3-
thiazolidin-3-yl]-5-methoxybenzamide (8d)
C19H19BrN2O5S, m.p. 182–184, yield: 78 %; FT-IR (KBr)
cm-1: 3464.4 (NH Stretch), 1712.7 (C=O stretch), 1561.6
(NH bend), 1480.0 (C=C of aromatic ring), 764.6 ([C–Br),
735.6 (C–Cl). 1H-NMR: (CDCl3, d/ppm, 400 MHz), 11.80
(s, 1H, [NH), 6.84–7.68(m, 6H, ArH), 5.94 (s, 1H, CH,
thiazolidinone ring), 4.0 (m, 2H, CH2, thiazolidinone ring),
3.84 (s, 3H, OCH3, 2,4-dimethoxy benzyl), 3.75 (s,
–OCH3, 2,4-dimethoxy benzyl). 3.73 (s, 3H, OCH3). LCMS
m/z: 468 (m ? 1, mol. wt. = 467.33, C19H19BrN2O5S).
2-Bromo-N-[2-(3-chlorophenyl)-4-oxo-1,3-thiazolidin-
3-yl]-5-methoxybenzamide (8a)
C17H14BrClN2O3S, m.p. 144–146, yield: 89 %; FT-IR
(KBr) cm-1: 3461.2 (NH Stretch), 1722.3 (C=O stretch),
1562.0 (NH bend), 1473.4 (C=C of aromatic ring), 764.6
([C–Br), 731.8 (C–Cl). 1H-NMR: (CDCl3, d/ppm,
400 MHz), 7.92 (s, 1H, NH), 7.5 (d, 1H, ArH,
J = 7.29 Hz), 7.26–7.40 (m, 4H, ArH), 7.04 (d, 1H, ArH,
J = 2.9 Hz), 6.79–6.82 (dd, 1H, ArH, J = 2.9 and 2.9 Hz),
6.55 (s, –CH, thiazolidinone ring), 3.80 (s, 2H, CH2, thia-
zolidinone ring), 3.74 (s, 3H, OCH3). 13CNMR (100 MHz,
CDCl3): 169.82, 165.34, 158.83, 134.90, 134.77, 134.33,
133.97, 130.47, 130.37, 128.99, 127.67, 118.93, 115.14,
109.57, 59.38 (CH carbon of thiazolidinone ring), 55.71
(OCH3 carbon of bromophenyl ring), 29.80 (CH2 carbon of
thiazolidinone ring). 13CNMR-DEPT-135 (100 MHz,
CDCl3): 134.33, 130.48, 130.37, 128.99, 127.67, 118.93,
115.13, 59.39 (CH carbon of thiazolidinone ring), 55.71
(OCH3 carbon of bromophenyl ring), 29.80 (CH2 carbon of
thiazolidinone ring). LCMS m/z: 443 (m ? 1, mol. wt. =
441.7, C17H14BrClN2O3S).
2-Bromo-5-methoxy-N-[2-(4-methoxyphenyl)-4-oxo-
1,3-thiazolidin-3-yl] benzamide (8e)
C18H17BrN2O4S, m.p. 128–130, yield: 80 %; FT-IR (KBr)
cm-1: 3215.9 (NH Stretch), 1715.2 (C=O stretch), 1600.8
(NH bend), 1569.0 (C=C of aromatic ring), 764.1 ([C–Br),
736.2 (C–Cl). 1H-NMR: (CDCl3, d/ppm, 400 MHz), 10.60
(s, 1H, NH), 7.27–7.49 (m, 3H, ArH), 6.88–6.96 (m, 3H,
ArH), 6.631–6.638 (d, 1H, ArH, J = 2.8 Hz), 5.87 (s, 1H,
CH, thiazolidinone ring), 3.84–3.89 (m, 2H, CH2, thiazo-
lidinone ring), 3.69–3.89 (m, 6H, 2 –OCH3 of p-methoxy
benzyl and 2-bromo-5-methoxy benzyl). LCMS m/z: 437,
438 (m, m ? 1, mol. wt. = 437.3, C18H17BrN2O4S).
2-Bromo-N-[2-(4-chlorophenyl)-4-oxo-1,3-thiazolidin-
3-yl]-5-methoxybenzamide (8b)
2-Bromo-5-methoxy-N-[2-(2-methoxyphenyl)-4-oxo-
1,3-thiazolidin-3-yl] benzamide (8f)
C17H14BrClN2O3S, m.p. 208–210, yield: 86 %; FT-IR (KBr)
cm-1: 3458.8 (NH Stretch), 1721.4 (C=O stretch), 1559.5
(NH bend), 1471.0 (C=C of aromatic ring), 764.9 ([C–Br),
730.7 (C–Cl). 1H-NMR: (CDCl3, d/ppm, 400 MHz), 10.67
(s, 1H, NH), 7.43–7.53 (m, 5H, ArH), 6.94–6.97 (m, 1H,
ArH), 6.677–6.684 (d, 1H, ArH, J = 2.8 Hz), 5.91 (s, 1H,
CH, thiazolidinone ring), 3.77–3.95 (m, 2H, CH2, thiazo-
lidinone ring), 3.70 (s, 3H, OCH3). LCMS m/z: 443 (m ? 1,
mol. wt. = 441.7, C17H14BrClN2O3S).
C18H17BrN2O4S, m.p. 134–136, yield: 80 %; FT-IR (KBr)
cm-1: 3220.7 (NH Stretch), 1723.6 (C=O stretch), 1601.5
(NH bend), 1570.6 (C=C of aromatic ring), 769.4 ([C–Br),
740.5 (C–Cl). 1H-NMR: (CDCl3, d/ppm, 400 MHz), 10.67
(s, 1H, NH), 7.30–7.46 (m, 3H, ArH), 6.89–6.98 (m, 3H,
ArH), 6.638–6.645 (d, 1H, ArH, J = 2.8 Hz), 5.92 (s, 1H,
CH, thiazolidinone ring), 3.88–3.93 (m, 2H, CH2, thiazo-
lidinone ring), 3.71–3.94 (m, 6H, 2 –OCH3 of p-methoxy
benzyl and 2-bromo-5-methoxy benzyl). LCMS m/z: 438
(m ? 1, mol. wt. = 437.3, C18H17BrN2O4S).
2-Bromo-N-[2-(2-chlorophenyl)-4-oxo-1,3-thiazolidin-
3-yl]-5-methoxybenzamide (8c)
2-Bromo-5-methoxy-N-[2-(4-nitrophenyl)-4-oxo-1,3-
thiazolidin-3-yl] benzamide (8g)
C17H14BrClN2O3S, m.p. 152–154, yield: 75 %; FT-IR
(KBr) cm-1: 3458.9 (NH Stretch), 1716.9 (C=O stretch),
1559.7 (NH bend), 1475.2 (C=C of aromatic ring), 765.1
C17H14BrN3O5S, m.p. 150–152, yield: 74 %; FT-IR (KBr)
cm-1: 3432.6 (NH Stretch), 1726.8 (C=O stretch), 1560.42
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