JOURNAL OF SULFUR CHEMISTRY
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2-(4-chloro-3-nitrophenyl)-3-(p-tolyl)thiazolidin-4-one (4i)
Yellow powder. M.p. 146–148°C. Yield: 0.32 g (85%). FT-IR (KBr, ν, cm−1): 2922, 1714,
1605, 1518, 1350, 1134, 807. 1H NMR (400 MHz, DMSO-d6, δ, ppm): 7-8.77 (m, 7H), 6.78
(s, 1H), 3.41 (m, 2H), 2.5 (s, 3H). 13C NMR (100 MHz, DMSO-d6, δ, ppm): 20.23, 31.83,
68.7, 120.59, 129.82, 134.22, 139.34, 141.74, 150.59, 179.28. Mass (m/z): 348. Anal. Calcd.
For C16H13ClN2O3S: C, 55.1; H, 3.76; N, 8.03. Found: C, 55.04; H, 3.85; N, 7.98.
2-(4-chloro-3-nitrophenyl)-3-phenylthiazolidin-4-one (4j)
Yellow powder. M.p. 153–155°C. Yield: 0.29 g (80%). FT-IR (KBr, ν, cm−1): 2923, 1714,
1607, 1534, 1344, 1138, 735. 1H NMR (400 MHz, DMSO-d6, δ, ppm): 6.87-8.35 (m, 8H),
6.61 (s, 1H), 3.49 (m, 2H). 13C NMR (100 MHz, DMSO-d6, δ, ppm): 30.13, 60.17, 123.99,
129.8, 133.55, 136.61, 139.01, 142.41, 147.24, 172.46. Mass (m/z): 334. Anal. Calcd. For
C15H11ClN2O3S: C, 53.82; H, 3.31; N, 8.37. Found: C, 53.75; H, 3.37; N, 8.31.
2-(furan-2-yl)-3-phenylthiazolidin-4-one (4k)
Yellow powder. M.p. 138–140°C. Yield: 0.24 g (88%). 1H NMR (400 MHz, DMSO-d6, δ,
ppm): 6.26–7.79 (m, 8H), 5.79 (s, 1H), 3.29–379 (m, 2H). 13C NMR (100 MHz, DMSO-d6,
δ, ppm): 30.62, 48.88, 112.92, 115.65, 117.59, 124.96, 127.66, 130.79, 143.98, 145.52, 188.62.
2-(4-methoxyphenyl)-3-(p-tolyl)thiazolidin-4-one (4l)
Yellow powder. M.p. 130–132°C. Yield: 0.29 g (89%). FT-IR (KBr, ν, cm−1): 2960, 1672,
1591, 1496, 1438, 1393, 746. 1H NMR (400 MHz, DMSO-d6, δ, ppm): 6.77-7.36 (m, 8H),
5.3 (s, 1H), 3.84 (m, 2H), 3.41 (s, 3H), 2.57 (s, 3H). 13C NMR (100 MHz, DMSO-d6, δ,
ppm): 20.57, 31.15, 60.51, 71.77, 117.5, 125, 127.41, 130.13, 135.26, 138.32, 161.88, 172.47.
Mass (m/z): 299. Anal. Calcd. For C17H17NO2S: C, 68.2; H, 5.72; N, 4.68. Found: C, 68.11;
H, 5.79; N, 4.59.
2-(2-chlorophenyl)-3-(p-tolyl)thiazolidin-4-one (4m)
White powder. M.p. 128–131°C. Yield: 0.31 g (93%). FT-IR (KBr, ν, cm−1): 2919, 1691,
1609, 1518, 1439, 807. 1H NMR (400 MHz, DMSO-d6, δ, ppm): 8.87 (s, 1H), 6.73-7.48 (m,
7H), 6.5 (s, 1H), 3.32 (m, 2H), 2.5 (s, 3H). 13C NMR (100 MHz, DMSO-d6, δ, ppm): 19.79,
31.36, 69.41, 103.76, 114.74, 119.02, 120.14, 124.27, 129.47, 130.59, 135.43, 139.54, 178.71.
Mass (m/z): 303. Anal. Calcd. For C16H14ClNOS: C, 63.26; H, 4.65; N, 4.61. Found: C,
63.18 H, 4.72; N, 4.54.
2-(2-bromophenyl)-3-(p-tolyl)thiazolidin-4-one (4n)
Cream powder. M.p. 136–138°C. Yield: 0.34 g (90%). FT-IR (KBr, ν, cm−1): 2906,
1715, 1609, 1518, 1439, 807. 1H NMR (400 MHz, DMSO-d6, δ, ppm): 7.47–7.59 (m, 2H),
6.31–7.04 (m, 6H), 5.76 (s, 1H), 3.25 (m, 2H), 2.51 (s, 3H). 13C NMR (100 MHz, DMSO-d6,
δ, ppm): 19.9, 30.82, 67.34, 113.41, 117.52, 129.11, 132.86, 135.58, 139.02, 145.84, 148.24,
151.31, 178.95. Mass (m/z): 347. Anal. Calcd. For C16H14BrNOS: C, 55.18; H, 4.05; N,
4.02. Found: C, 55.09; H, 4.14; N, 3.98.
Acknowledgements
We would like to thank Bu-Ali Sina University, Center of Excellence in Development of Envi-
ronmentally Friendly Methods for Chemical Synthesis (CEDEFMCS) for financial support of this
study.
Disclosure statement
No potential conflict of interest was reported by the author(s).