Molecular Diversity
2‑(2‑Chlorophenoxy)‑N‑(4‑oxo‑2‑phenylthiazolidin‑3‑yl)
benzamide (5j) 5j (0.4 g, 55%) was synthesized by gen-
eral procedure using a mixture of compound 4b (1g,
3.8 mmol), benzaldehyde (0.38 ml, 3.8 mmol) and thiogly-
colic acid (0.53 ml, 7.6 mmol); mp: 104–106 °C; IR (KBr)
2‑(2‑Chlorophenoxy)‑N‑(2‑(4‑nitrophenyl)‑4‑oxothiazoli‑
din‑3‑yl)benzamide (5m) 5m (0.5 g, 33%) was synthesized
by general procedure using a mixture of compound 4b (1 g,
3.8 mmol), 4-chlorobenzaldehyde (0.44 ml, 3.8 mmol) and
thioglycolic acid (0.53 ml, 7.6 mmol); mp: 149–151 °C; IR
(KBr) (νmax, cm−1): 1343,1530 (NO2), 1682 (C=O), 1718
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(νmax, cm−1): 1651 (C=O), 1726 (C=O), 3326 (NH); H
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NMR (500 MHz, CDCl3): δ = 3.83 (2d, J = 15.9 Hz, 2H,
CH2), 6.08 (s, 1H, Ar–CH), 6.61 (d, J = 8.3 Hz,1H, aro-
matic), 6.86 (dd, J = 7.9,1.0 Hz, 1H, aromatic), 7.30–7.44
(m, 9H, aromatic), 7.63 (d, J = 8.0 Hz, 1H, aromatic),
8.20 (dd, J = 7.9,1.7 Hz, 1H, aromatic), 9.06 (s, 1H, NH);
13C NMR (100 MHz, CDCl3): δ = 30.25, 62.92, 115.86,
118.33, 120.45, 120.75, 122.05, 125.99, 126.41, 127.84,
128.53, 129.28, 133.68, 139.05, 149.59, 152.22, 155.13,
155.13, 163.44, 169.60; Anal. calcd for C22H17ClN2O3S:
C 62.19, H 4.03, N 6.59, found: C 62.49, H 4.27, N 6.31.
(C=O), 3220 (NH); H NMR (500 MHz, CDCl3): δ=3.8
(dd, J=15.9 Hz, 2H, CH2), 6.15 (s, 1H, Ar–CH), 6.67 (d,
J=8.3 Hz, 1H, aromatic), 6.81 (d, J=8.01 Hz, 1H, aro-
matic), 7.13–7.20 (m, 1H, aromatic), 7.21–7.27 (m, 2H,
aromatic), 7.39 (dd, J=7.9,1.3 Hz, 1H, aromatic), 7.40
(t, 1H, aromatic), 7.57 (d, J=8.5 Hz, 2H, aromatic), 8.10
(d, J=8.5 Hz, 2H, aromatic), 8.18 (dd, J=7.8,1.6 Hz, 1H,
aromatic), 9.01 (s, 1H, NH); 13C NMR (100 MHz, CDCl3):
δ=30.09, 61.79, 116.71, 120.72, 120.81, 124.07, 124.14,
125.46, 126.34, 128.28, 128.87, 130.99, 132.64, 134.14,
144.15, 148.19, 149.67, 154.58 163.53, 169.34; Anal. calcd
for C22H16ClN3O5S: C 56.23, H 3.43, N 8.94, found: C
56.57, H 3.66, N 8.72.
2‑(2‑Chlorophenoxy)‑N‑(2‑(4‑hydroxyphenyl)‑4‑oxothia‑
zolidin‑3‑yl)benzamide (5k) 5k (0.5 g, 52%) was synthe-
sized by general procedure using a mixture of compound
4b (1g, 3.8 mmol), 4-hydroxybenzaldehyde (0.46 g,
3.8 mmol) and thioglycolic acid (0.53 ml, 7.6 mmol);
mp: 93–95 °C; IR (KBr) (νmax, cm−1): 1667 (C=O), 1710
2‑(2‑Chlorophenoxy)‑N‑(2‑(4‑chlorophenyl)‑4‑oxothiazoli‑
din‑3‑yl)benzamide (5n) 5n (0.45 g, 48%) was synthesized
by general procedure using a mixture of compound 4b (1 g,
3.8 mmol), 4-nitrobenzaldehyde (0.57 g, 3.8 mmol) and
thioglycolic acid (0.53 ml, 7.6 mmol); mp: 132–134 °C; IR
(KBr) (νmax, cm−1): 1659 (C=O), 1710 (C=O), 3360 (NH);
1H NMR (500 MHz, CDCl3): δ=3.85 (dd, J=15.9 Hz,
2H, CH2), 6.04 (s, 1H, Ar–CH), 6.66 (d, J=8.3 Hz, 1H,
aromatic), 6.85 (dd, J=7.9,0.9 Hz, 1H, aromatic), 7.18 (d,
J=8.4 Hz, 2H, aromatic), 7.22–7.30 (m, 3H, aromatic),
7.32 (d, J=8.3 Hz, 2H, aromatic), 7.41–7.46 (m, 1H, aro-
matic), 7.45 (dd, J=7.9,1.6 Hz, 1H, aromatic), 8.20 (dd,
J=7.9,1.6 Hz, 1H, aromatic), 9.02 (s, 1H, NH); 13C NMR
(100 MHz, CDCl3): δ=30.17, 62.23, 116.41, 120.72,
120.81, 124.07, 124.14, 125.46, 126.34, 128.28), 128.87,
130.99, 132.64, 134.14, 144.15, 148.19, 149.67, 154.58,
163.53, 169.34; Anal. calcd for C22H16Cl2N2O3S: C 57.52,
H 3.51, N 6.10, found: C 57.76, H 3.68, N 5.57.
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(C=O), 3380 (OH, NH); H NMR (500 MHz, CDCl3):
δ = 3.8 (dd, J = 15.2 Hz, 2H, CH2), 6.01 (s, 1H, Ar–CH),
6.63 (d, J = 8.3 Hz, 1H, aromatic), 6.66 (d, J = 8.5 Hz, 2H,
aromatic), 6.88 (d, J = 7.1 Hz, 1H, aromatic), 7.21–7.30
(m, 5H, aromatic), 7.38–7.40 (m, 1H, aromatic), 7.45 (dd,
J = 7.9,1.5 Hz, 1H, aromatic), 8.20 (dd, J = 7.9,1.6 Hz,
1H, aromatic), 9.03 (s, 1H, NH); 13C NMR (100 MHz,
CDCl3): δ = 30.29, 62.65, 115.72, 116.08, 120.50, 121.84,
123.70, 126.28, 126.35, 128.22, 128.33, 129.61, 130.98,
132.70, 133.87, 149.69, 155.08, 156.74, 163.47, 169.52;
Anal. calcd for C22H17ClN2O4S: C 62.19, H 4.03, N 6.59,
found: C 62.46, H 4.24, N 6.35.
N‑(2‑(2‑bromophenyl)‑4‑oxothiazolidin‑3‑yl)‑2‑(2‑chloro‑
phenoxy)benzamide (5l) 5l (0.44 g, 47%) was synthesized
by general procedure using a mixture of compound 4b (1 g,
3.8 mmol), 2-bromobenzaldehyde (0.44 ml, 3.8 mmol) and
thioglycolic acid (0.53 ml, 7.6 mmol); mp: 89–91 °C; IR
(KBr) (νmax, cm−1): 1674 (C=O), 1709 (C=O), 3154 (NH);
1H NMR (500 MHz, CDCl3): δ=3.84 (dd, J=15.8 Hz, 2H,
CH2), 6.53 (s, 1H, Ar–CH), 6.67 (d, J=8.3 Hz, 1H, aro-
matic), 6.97 (dd, J=8.0,1.1 Hz, 1H, aromatic), 7.03 (t, 1H,
aromatic), 7.20–7.44 (m, 7H, aromatic), 7.51 (d, J=7.8 Hz,
1H, aromatic), 8.23 (dd, J=7.9,1.7 Hz, 1H, aromatic), 9.13
(s, 1H, NH); 13C NMR (100 MHz, CDCl3): δ=29.71, 61.93,
116.16, 120.75, 121.77, 123.55, 123.81, 126.18, 126.28,
128.14, 128.20, 128.36, 130.21, 130.91, 132.81, 133.34,
133.87, 136.50, 149.82, 154.99, 163.48, 169.69; Anal. calcd
for C22H16BrClN2O3S: C 52.45, H 3.20, N 5.56, found: C
52.80, H 3.49, N 5.31.
2‑(2‑Chlorophenoxy)‑N‑(2‑(4‑methoxyphenyl)‑4‑oxothia‑
zolidin‑3‑yl)benzamide (5o) 5o (0.4 g, 42%) was synthe-
sized by general procedure using a mixture of compound
4b (1 g, 3.8 mmol), 4-methoxybenzaldehyde (0.43 ml,
3.8 mmol) and thioglycolic acid (0.53 ml, 7.6 mmol); mp:
118–120 °C; IR (KBr) (νmax, cm−1): 1658 (C=O), 1708
(C=O), 3353 (NH); 1H NMR (500 MHz, CDCl3): δ = 3.72
(s, 3H, OCH3), 3.84 (dd, J = 15.9 Hz, 2H, CH2), 6.03 (s,
1H, Ar–CH), 6.61 (d, J = 8.3 Hz, 1H, aromatic), 6.72 (d,
J = 8.7 Hz, 2H, aromatic), 6.88 (dd, J = 8.09,1.0 Hz, 1H,
aromatic), 7.20 (dd, J = 7.9,1.7 Hz, 1H, aromatic), 7.19–
7.24 (m, 3H, aromatic), 7.32 (d, J = 8.6 Hz, 2H, aromatic),
7.33–7.42 (m, 1H, aromatic), 7.44 (dd, J = 7.9,1.6 Hz, 1H,
aromatic), 8.20 (dd, J = 7.89,1.7 Hz, 1H, aromatic), 8.99
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