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P. PATHAK ET AL.
2-(4-bromophenyl)-3-(5-phenyl-1,3,4-thiadiazol-2-yl)thiazolidin-4-one (4a)
Physical state: Light yellow powder; Yield 82%; Mol wt:418.33; mp 186–188 ꢂC; Rf: 0.88
(benzene: ethyl acetate); Solubility: Ethanol, Chloroform, DMSO-d6; FT-IR Spectra
(KBr) in cmꢀ1: 2923 (N–CH–Sstretch, thiazolidinone), 1618 (C¼Ostretch), 1569 (C¼C
ringstretch, Ar), 1517–1431 (–C¼Nstretch), 1400–1089 (–C–H in planedef, Ar), 1385
(C¼Cstretch), 1239 (C–Nstretch), 1176 (N–Nstretch), 695 (C–S–Cstretch, thiadizolestretch), 616
1
(C–Brstretch); H-NMR (400 MHz, DMSO-d6, TMS) d ppm: 3.17 (dd, 2H, CH2, thiazoli-
dinone ring), 5.98 (s, 1H, CH, thiazolidinone ring), 7.17–7.19 (d, 1–H, CH, Br-Ph),
7.22–7.25 (d, 1H, CH, Ph), 7.27–7.28 (d, 1H, CH, Br-Ph), 7.36–7.36 (d, 1H, CH, Br-
Ph), 7.38–7.39 (d, 1H, CH, Ph), 7.46–7.47 (d, 1H, CH, Ph); 13C NMR (100 MHz,
CDCl3) d ppm: 170.7, 165.5, 161.3, 136.0, 131.5, 130.2, 130.1, 128.9, 126.6, 120.9, 68.7,
34.0; Mass: 418.96 (M þ H)þ; Elemental analysis for C17H12BrN3OS2, Calculated: C,
48.81; H, 2.89; N, 10.05. Found: C, 48.65; H, 2.59; N, 10.18.
2-(4-bromophenyl)-3-(5-(4-nitrophenyl)-1,3,4-thiadiazol-2-yl)thiazolidin-4-one(4b)
Physical state: Yellowish white powder; Yield 80%; Mol wt: 463.33; mp 187–189 ꢂC; Rf:
0.86 (benzene: ethyl acetate); Solubility: Ethanol, Chloroform, DMSO-d6; FT-IR Spectra
(KBr) in cmꢀ1: 3272 (N–CH–Sstretch, thiazolidinone), 2297 (C–Hstretch, Ar), 1627
(C¼Ostretch), 1627–1483 (–C¼Nstretch), 1570 (C¼C ringstretch, Ar), 1400–1093 (–C–H in
planedef, Ar), 1385 (NO2 stretch), 1235 (C–Nstretch), 1173 (N–Nstretch), 696 (C–S–Cstretch
,
1
thiadizole), 638 (C–Brstretch). H-NMR (400 MHz, DMSO-d6, TMS) d ppm: 3.18 (dd,
2H, CH2, thiazolidinone ring), 5.90 (s, 1H, CH, thiazolidinone ring), 7.49–7.50 (d, 1H,
CH, Br-Ph), 7.52–7.54 (d, 1H, CH, Br-Ph), 7.56–7.57 (d, 1H, CH, Br-Ph), 7.83 (d, 1H,
CH, NO2-Ph), 7.85 (d, 1H, CH, NO2-Ph), 7.93–7.94 (d, 1H, CH, NO2-Ph); 13C NMR
(100 MHz, CDCl3) d ppm: 174.2, 171.1, 163.2, 139.6, 138.2, 135.5, 134.9, 128.6, 128.4,
124.6, 124.1, 121.6, 68.7, 34.0; Mass Spectra: 463.94 (M þ H)þ; Elemental analysis for
C17H11BrN4O3S2, Calculated: C, 44.07; H, 2.39; N, 12.09; Found: C, 44.21; H, 2.16;
N, 12.14.
2-(4-bromophenyl)-3-(5-(4-hydroxyphenyl)-1,3,4-thiadiazol-2-yl)thiazolidin-4-
one (4c)
Physical state: Yellowish powder; Yield 77%; Mol wt: 434.96; mp 188–190 ꢂC; Rf: 0.88
(benzene: ethyl acetate); Solubility: Ethanol, Chloroform, DMSO-d6; FT-IR spectra
(KBr) in cmꢀ1
:
2919 (N–CH–Sstretch
,
thiazolidinone), 1623 (C¼Ostretch), 1583
(C¼Cstretch, Ar), 1500–1435 (–C¼Nstretch), 1400–1083 (–C–H in planedef, Ar), 1247
(C–OHstretch, Ar), 1154 (C–Nstretch), 1114 (N–Nstretch), 688 (C–S–C thiadizolestretch), 660
1
(C–Brstretch): H-NMR (400 MHz, DMSO-d6, TMS) d ppm: 3.82, 3.94 (dd, 2H, CH2,
thiazolidinone ring), 6.24 (s, 1H, CH, thiazolidinone ring), 6.61–6.63 (d, 1H, CH,
hydroxy-Ph), 7.14–7.16 (d, 1H, CH, hydroxy-Ph), 7.36–7.38 (d, 1 H, CH, Br-Ph),
7.42–7.44 (d, 1H, CH, hydroxy-Ph), 7.50–7.55 (d, 1–H, CH, Br-Ph), 7.77–7.79 (d, 1 H,
CH, Br-Ph); 13C NMR (100 MHz, CDCl3) d ppm: 170.7, 165.3, 159.6, 154.0, 136.0,
131.5, 129.1, 128.9, 122.3, 120.9, 115.0, 68.7, 34.0; Mass Spectra: 355.04 (M þ H)þ;