Paper
NJC
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1669 (CQO), 1632 (CQN), 1330, 1152 (SO2); H NMR (DMSO-d6) aromatic), 1676 (CQO), 1632 (CQN), 1332, 1161 (SO2); H NMR
d/ppm: 12.65 (s, 1H, CON-H), 10.13 (s, 1H, SO2N-H), 7.96 (s, (DMSO-d6) d/ppm: 12.75 (s, 1H, CON-H), 10.35 (s, 1H, SO2N-H),
1H, QC–H), 7.68–7.83 (m, 1H, Ar-H), 7.64–7.67 (m, 4H, Ar-H), 7.81–7.95 (m, 3H, Ar-H), 7.62–7.71 (d, 3H, Ar-H), 7.44–7.56 (m,
7.54–7.59 (m, 4H, Ar-H), 7.41–7.43 (d, 1H, J = 8.8 Hz, Ar-H), 4H, Ar-H), 7.17–7.19 (d, 1H, J = 8 Hz, Ar-H); HRMS-ESI (m/z)
7.31–7.33 (d, 1H, J = 8.8 Hz, Ar-H), 7.16–7.18 (d, 1H, J = 7.6 Hz, calcd (M + H)+ 571.9231; found 571.9226; anal. calcd for
Ar-H); HRMS-ESI (m/z) calcd (M + H)+ 488.0320; found 488.0300; C22H13N3S2O3Cl4: C, 46.09; H, 2.29; N, 7.33; S, 11.19; found: C,
anal. calcd for C22H15N3S2O3ClF: C, 54.15; H, 3.10; N, 8.61; S, 13.14; 46.05; H, 2.25; N, 7.30; S, 11.09.
found: C, 54.02; H, 3.04; N, 8.56; S, 13.32.
(Z)-4-(5-(3-Chlorobenzylidene)-4-oxothiazolidin-2-ylideneamino)-
(Z)-4-(5-(4-Chlorobenzylidene)-4-oxothiazolidin-2-ylideneamino)- N-(2,4,5-trichloro phenyl)benzenesulfonamide (7c). Yield 83%; m.p.
N-(2,4-dichlorophenyl)benzenesulfonamide (6g). Yield 73%; m.p. 291–293 1C; IR, (KBr, cmÀ1): 3267, 3132 (N–H), 2977 (C–H
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262–264 1C; IR (KBr, cmÀ1): 3282, 3156 (N–H), 2968 (C–H aromatic), aromatic), 1731 (CQO), 1647 (CQN), 1332, 1163 (SO2); H NMR
1714 (CQO), 1652 (CQN), 1336, 1155 (SO2); 1H NMR (DMSO-d6) (DMSO-d6) d/ppm: 12.70 (s, 1H, CON-H), 10.37 (s, 1H, SO2N-H),
d/ppm: 12.64 (s, 1H, CON-H), 10.59 (s, 1H, SO2N-H), 7.94 (s, 7.96 (s, 1H,QC–H), 7.79–7.82 (d, 2H, Ar-H), 7.67–7.73 (t, 3H, Ar-H),
1H, QC–H), 7.76–7.81 (t, 2H, Ar-H), 7.52–7.66 (t, 4H, Ar-H), 7.60 (s, 1H, Ar-H), 7.45–7.50 (m, 3H, Ar-H), 7.19–7.21 (d, 1H, J =
7.28–7.30 (d, 1H, J = 6.8 Hz, Ar-H), 7.18–7.20 (d, 1H, J = 6.4 Hz, 6.4 Hz, Ar-H); HRMS-ESI (m/z) calcd (M + H)+ 571.9231; found
Ar-H), 6.87–6.96 (m, 3H, Ar-H); HRMS-ESI (m/z) calcd (M + Na)+ 571.9228; anal. calcd for C22H13N3S2O3Cl4: C, 46.09; H, 2.29; N,
559.9428; found 559.9404; anal. calcd for C22H14N3S2O3Cl3: C, 7.33; S, 11.19; found: C, 46.04; H, 2.23; N, 7.32; S, 11.08.
49.04; H, 2.62; N, 7.80; S, 11.90; found: C, 48.95; H, 2.44; N,
7.68; S, 11.82.
(Z)-4-(5-(4-(Dimethylamino)benzylidene)-4-oxothiazolidin-2-
ylideneamino)-N-(2,4,5-tri chlorophenyl)benzenesulfonamide
(Z)-4-(5-(4-Chlorobenzylidene)-4-oxothiazolidin-2-ylideneamino)- (7d). Yield 83%; m.p. 291–293 1C; IR (KBr, cmÀ1): 3346, 3132
N-(3-chloro-4-fluoro phenyl)benzenesulfonamide (6h). Yield 73%; (N–H), 2924 (C–H aromatic), 1662 (CQO), 1587 (CQN), 1332,
m.p. 273–275 1C; IR (KBr, cmÀ1): 3259, 3091 (N–H), 2983 (C–H 1163 (SO2); H NMR (DMSO-d6) d/ppm: 12.32 (s, 1H, CON-H),
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aromatic), 1728 (CQO), 1662 (CQN), 1325, 1153 (SO2); H NMR 10.34 (s, 1H, SO2N-H), 7.96 (s, 1H, QC–H), 7.84 (s, 1H, Ar-H),
(DMSO-d6) d/ppm: 12.64 (s, 1H, CON-H), 10.48 (s, 1H, SO2N-H), 7.73 (s, 2H, Ar-H), 7.54 (s, 1H, Ar-H), 7.45 (s, 2H, Ar-H), 7.34 (s,
7.94 (s, 1H, QC–H), 7.74–7.80 (m, 2H, Ar-H), 7.63–7.66 (d, 2H, 1H, Ar-H), 7.19 (s, 1H, Ar-H), 6.77 (s, 2H, Ar-H), 2.98 (s, 6H,
Ar-H), 7.53 (s, 3H, Ar-H), 7.32–7.36 (t, 1H, J = 8.4 Hz, Ar-H), 7.18– –NCH3); HRMS-ESI (m/z) calcd (M + H)+ 581.0025; found
7.20 (d, 2H, J = 8.8 Hz, Ar-H),7.09 (s, 1H, Ar-H); HRMS-ESI (m/z) 581.0036; anal. calcd for: C, 49.54; H, 3.29; N, 9.63; S, 11.02;
calcd (M + H)+ 543.9724; found 543.9730; anal. calcd for found: C, 49.48; H, 3.23; N, 9.58; S, 10.86.
C
22H14N3S2O3Cl2F: C, 50.58; H, 2.70; N, 8.04; S, 12.28; found:
(Z)-4-(5-(4-Hydroxybenzylidene)-4-oxothiazolidin-2-ylideneamino)-
N-(2,4,5-trichloro phenyl)benzenesulfonamide (7e). Yield 79%; m.p.
C, 50.52; H, 2.64; N, 7.96; S, 12.02.
(Z)-4-(5-(4-Chlorobenzylidene)-4-oxothiazolidin-2-ylideneamino)- 295–297 1C; IR (KBr, cmÀ1): 3500 (OH), 3274, 3199 (N–H), 2981
N-(2,4,5-trichloro phenyl)benzenesulfonamide (6i). Yield 83%; m.p. (C–H aromatic), 1662 (CQO), 1587 (CQN), 1326, 1164 (SO2);
293–295 1C; IR (KBr, cmÀ1): 3272, 3093 (N–H), 2970 (C–H aromatic), 1H NMR (DMSO-d6) d/ppm: 12.45 (s, 1H, CON-H), 10.35 (s, 1H,
1722 (CQO), 1641 (CQN), 1326, 1153 (SO2); 1H NMR (DMSO-d6) SO2N-H), 10.23 (s, 1H, OH), 7.96 (s, 1H, QC–H), 7.84 (s, 1H,
d/ppm: 12.65 (s, 1H, CON-H), 10.37 (s, 1H, SO2N-H), 7.96 (s, 1H, Ar-H), 7.71–7.72 (d, 2H, J = 4.8 Hz, Ar-H), 7.58 (s, 1H, Ar-H), 7.45
QC–H), 7.85 (s, 1H, Ar-H), 7.64–7.78 (m, 4H, Ar-H), 7.54 (s, 3H, (s, 1H, Ar-H), 7.37 (s, 2H, Ar-H), 7.19 (s, 1H, Ar-H), 6.88 (s, 2H,
Ar-H), 7.47 (s, 1H, Ar-H), 7.18–7.20 (d, 1H, J = 6.8 Hz, Ar-H); 13
C
Ar-H); HRMS-ESI (m/z) calcd (M + H)+ 553.9559; found 553.9564;
NMR (DMSO): d = 171.91, 167.14, 152.15, 135.53, 134.90, 134.54, anal. calcd for C22H14N3S2O4Cl3: C, 47.62; H, 2.54; N, 7.57; S,
133.80, 132.13, 131.24, 131.10, 130.96, 130.06, 129.41, 129.24, 11.56; found: C, 47.57; H, 2.48; N, 7.51; S, 11.46.
128.69, 128.36, 123.42, 121.96. HRMS-ESI (m/z) calcd (M + H)+
(Z)-4-(5-(3,4,5-Trimethoxybenzylidene)-4-oxothiazolidin-2-
571.9231; found 571.9228; anal. calcd for C22H13N3S2O3Cl4: C, ylideneamino)-N-(2,4,5-trichlorophenyl)benzenesulfonamide (7f).
46.09; H, 2.29; N, 7.33; S, 11.19; found: C, 46.05; H, 2.25; N, 7.31; Yield 69%; m.p. 295–297 1C; IR, (KBr, cmÀ1): 3234, 3120 (N–H),
S, 11.04.
2964 (C–H aromatic), 1714 (CQO), 1645 (CQN), 1327, 1130 (SO2);
(Z)-4-(5-Benzylidene-4-oxothiazolidin-2-ylideneamino)-N-(2,4,5- 1H NMR (DMSO-d6) d/ppm: 12.57 (s, 1H, CON-H), 10.35 (s, 1H,
trichlorophenyl)benzene sulfonamide (7a). Yield 80%; m.p. 286– SO2N-H), 7.96 (s, 1H,QC–H), 7.83 (s, 1H, Ar-H), 7.65–7.79 (m, 3H,
288 1C; IR, (KBr, cmÀ1): 3247, 3132 (N–H), 2977 (C–H aromatic), Ar-H), 7.50 (s, 1H, Ar-H), 7.20 (s, 1H, Ar-H), 6.98 (s, 1H, Ar-H), 6.83
1703 (CQO), 1658 (CQN), 1332, 1159 (SO2); 1H NMR (DMSO-d6) (s, 1H, Ar-H), 3.86 (s, 3H, –OCH3), 3.72–3.75 (d, 6H, –OCH3);
d/ppm: 12.62 (s, 1H, CON-H), 10.36 (s, 1H, SO2N-H), 7.96 (s, 1H, HRMS-ESI (m/z) calcd (M + H)+ 627.9928; found 627.9931; anal.
QC–H), 7.84 (s, 1H, Ar-H), 7.68–7.73 (t, 2H, Ar-H), 7.46–7.51 (m, calcd for C25H20N3S2O6Cl3: C, 47.74; H, 3.21; N, 6.68; S, 10.20;
6H, Ar-H), 7.19–7.21 (d, 2H, J = 6.4 Hz, Ar-H); HRMS-ESI (m/z) found: C, 47.68; H, 3.18; N, 6.62; S, 10.16.
calcd (M + H)+ 559.9440; found 559.9424; anal. calcd for
C22H14N3S2O3Cl3: C, 49.04; H, 2.62; N, 7.80; S, 11.90. Found: C,
49.0; H, 2.58; N, 7.71; S, 11.84.
Conclusion
(Z)-4-(5-(2-Chlorobenzylidene)-4-oxothiazolidin-2-ylideneamino)-
N-(2,4,5-trichloro phenyl)benzenesulfonamide (7b). Yield 73%; In the present study, a series of thiazolidinone derivatives
m.p. 286–288 1C; IR, (KBr, cmÀ1): 3361, 3190 (N–H), 3049 (C–H bearing the sulfonamide moiety were synthesized in good yield.
1608 | New J. Chem., 2019, 43, 1597--1610
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