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. 2020 Mar 31;14(1):25. doi: 10.1186/s13065-020-00678-2

Table 1.

The physicochemical, elemental and spectral characteristics of synthesized thiazolidine-2,4-dione derivatives

Compound Physicochemical and spectral characteristics
graphic file with name 13065_2020_678_Stra_HTML.gif 5-((E)-4-((E)-(phenylimino)methyl)benzylidene)thiazolidine-2,4-dione: m.p. °C: 260-262; Rf value: 0.60b; % yield: 80; IR (KBr pellets) cm−1: 3375.41 (N–H str., thiazolidine ring), 1742.41 (C=O str., thiazolidin-2,4-dione ring), 1696.11 (C=N str., imine group), 1414.1 (C=C str., aromatic ring), 1602.13 (C=C str., methylene group), 3044.78 (C–H str., aromatic ring), 2919.12 (C–H str., aliphatic), 1317.75 (C–N str., thiazolidine ring), 614.77 (C–S bend., thiazolidine ring); 1H-NMR (δ, DMSO): 6.52–7.75 (m, 9H, Ar–H), 7.77 (s, 1H, –CH=), 8.71(s, 1H, CH=N), 12.49 (s, 1H, NH); M. Formula: C17H12N2O2S; MS: m/z 308 (M+); Elemental analysis (CHN) Theoretical calc: C, 66.22; H, 3.92; N, 9.08 Found: C, 66.25; H, 3.90; N, 9.09
graphic file with name 13065_2020_678_Strb_HTML.gif 5-((E)-4-((E)-hydrazonomethyl)benzylidene)thiazolidine-2,4-dione: m.p. °C: 220–222; Rf value: 0.74c; % yield: 60; IR (KBr pellets) cm−1: 1740.11 (C=O str., thiazolidin-2,4-dione ring), 1682.74 (C=N str., imine group), 1412.68 (C=C str., aromatic ring), 1615.22 (C=C str., methylene group), 3197.24 (C–H str., aromatic ring), 2922.17 (C–H str., aliphatic), 1224.86 (C–N str., thiazolidine ring), 618.11 (C–S bend., thiazolidine ring); 1H-NMR (δ, DMSO): 6.58–7.79 (m, 4H, Ar–H), 7.81 (s, 1H, –CH=), 8.68(s, 1H, CH=N), 1.92 (s, 2H, NH2), 12.49 (s, 1H, NH); M. Formula: C11H9N3O2S; Elemental analysis (CHN) Theoretical calc: C, 53.43; H, 3.67; N, 16.99 Found: C, 53.45; H, 3.68; N, 16.95
graphic file with name 13065_2020_678_Strc_HTML.gif 5-((E)-4-((E)-(2-phenylhydrazono)methyl)benzylidene)thiazolidine-2,4-dione: m.p. °C: 308–310; Rf value: 0.8d; % yield: 78; IR (KBr pellets) cm−1: 3441.91 (N–H str., phenyl hydrazine group), 3286.35 (N–H str., thiazolidine ring), 1726.16 (C=O str., thiazolidin-2,4-dione ring), 1677.76 (C=N str., imine group), 1413.66 (C=C str., aromatic ring), 1584.3 (C=C str., methylene group), 3043.30 (C–H str., aromatic ring), 1328.68 (C–N str., thiazolidine ring), 613.72 (C–S bend., thiazolidine ring); 1H-NMR (δ, DMSO): 6.77–7.79 (m, 4H, Ar–H), 7.80 (s, 1H, –CH=), 7.88(s, 1H, CH=N), 10.61 (s, 1H, NH adjacent to phenyl ring), 12.49 (s, 1H, NH of thiazolidine ring); M. Formula: C17H13N3O2S; MS: m/z 323.9 (M+ + 1), 321.9 (M+ − 1); Elemental analysis (CHN) Theoretical calc: C, 63.14; H, 4.05; N, 12.99 Found: C, 63.16; H, 4.05; N, 12.98
graphic file with name 13065_2020_678_Strd_HTML.gif 5-((E)-4-((E)-((2-chlorophenyl)imino)methyl)benzylidene)thiazolidine -2,4-dione: m.p. °C: 292–294; Rf value: 0.71d; % yield: 70; IR (KBr pellets) cm−1: 3381.37 (N–H str., thiazolidine ring), 1741.97 (C=O str., thiazolidin-2,4-dione ring), 1694.84 (C=N str., imine group), 1505.9 (C=C str., aromatic ring), 1606.57 (C=C str., methylene group), 3044.79 (C–H str., aromatic ring), 2978.2 (C–H str., aliphatic), 1305.25 (C–N str., thiazolidine ring), 606.87 (C–S bend., thiazolidine ring), 750.70 (C–Cl bend., o-substitution on phenyl ring); 1H NMR (δ, DMSO): 6.77–7.79 (m, 4H, Ar–H), 7.80 (s, 1H, –CH=), 7.88(s, 1H, CH=N), 10.61 (s, 1H, NH adjacent to phenyl ring), 12.49 (s, 1H, NH of thiazolidine ring); M. Formula: C17H11ClN2O2S; Elemental analysis (CHN) Theoretical calc: C, 59.56; H, 3.23; N, 8.17 Found: C, 59.60; H, 3.25; N, 8.12
graphic file with name 13065_2020_678_Stre_HTML.gif 5-((E)-4-((E)-((3-chlorophenyl)imino)methyl)benzylidene) thiazolidine-2,4-dione: m.p. °C: 280–282; Rf value: 0.73d; % yield: 75; IR (KBr pellets) cm−1: 3381.59 (N–H str., thiazolidine ring), 1741.81 (C=O str., thiazolidin-2,4-dione ring), 1695.1 (C=N str., imine group), 1479.44 (C=C str., aromatic ring), 1596.41 (C=C str., methylene group), 3050.78 (C–H str., aromatic ring), 2978.82 (C–H str., aliphatic), 1308.79 (C–N str., thiazolidine ring), 594.24 (C–S bend., thiazolidine ring), 777.34 (C–Cl bend., m-substitution on phenyl ring); 1H NMR (δ, DMSO): 7.23–8.07 (m, 8H, Ar–H), 7.81 (s, 1H, –CH=), 8.68 (s, 1H, CH=N), 12.58 (s, 1H, NH); M. Formula: C17H11ClN2O2S; MS: m/z 341.43 (M+ − 1); Elemental analysis (CHN) Theoretical calc: C, 59.56; H, 3.23; N, 8.17 Found: C, 59.62; H, 3.23; N, 8.18
graphic file with name 13065_2020_678_Strf_HTML.gif 5-((E)-4-((E)-((furan-2-ylmethyl)imino)methyl)benzylidene) thiazolidine-2,4-dione: m.p. °C: 92–94; Rf value: 0.71a; % yield: 70; IR IR (KBr pellets) cm−1: 3328.11 (N–H str., thiazolidine ring), 1694.77 (C=O str., thiazolidin-2,4-dione ring), 1610.48 (C=N str., imine group), 1423.16 (C=C str., aromatic ring), 1548.31 (C=C str., methylene group), 3045.54 (C–H str., aromatic ring), 2975.08 (C–H str., aliphatic), 1306.66 (C–N str., thiazolidine ring), 603.55 (C–S bend., thiazolidine ring), 1159.90 (C–C str.), 1012.66 (C–O–C str., furan ring); 1H NMR (δ, DMSO): 7.18–7.88 (m, 4H, Ar–H), 7.78 (s, 1H, –CH=), 8.76 (s, 1H, CH=N), 12.48 (s, 1H, NH), 4.77 (d, 2H, –CH2 adjacent to furan ring), 6.30 (d, 1H, CH of furan ring at 3rd position), 6.42 (t, 1H, CH of furan ring at 4th position), 7.47 (d, 1H, CH of furan ring adjacent to O); M. Formula: C16H12N2O3S; MS: m/z 313.16 (M+ + 1); Elemental analysis (CHN) Theoretical calc: C, 61.53; H, 3.87; N, 8.97 Found: C, 61.55; H, 3.90; N, 8.95
graphic file with name 13065_2020_678_Strg_HTML.gif 5-((E)-4-((E)-(m-tolylimino)methyl)benzylidene)thiazolidine-2,4-dione: m.p. °C: 90–92; Rf value: 0.81a; % yield: 65; IR (KBr pellets) cm−1: 3378.54 (N–H str., thiazolidine ring), 1743.48 (C=O str., thiazolidin-2,4-dione ring), 1691.85 (C=N str., imine group), 1487.15 (C=C str., aromatic ring), 1602.26 (C=C str., methylene group), 3036.12 (C–H str., aromatic ring), 2967.46 (C–H str., aliphatic), 1321.95 (C–N str., thiazolidine ring), 597.53 (C–S bend., thiazolidine ring), 1154.43 (C–C str.); 1H NMR (δ, DMSO): 7.08–8.06 (m, 8H, Ar–H), 7.62 (s, 1H, –CH=), 8.43 (s, 1H, CH=N), 12.34 (s, 1H, NH), 2.14(s, 3H, CH3); M. Formula: C18H14N2O2S; MS: m/z 320.96 (M+ − 1); Elemental analysis (CHN) Theoretical calc: C, 67.06; H, 4.38; N, 8.69 Found: C, 67.09; H, 4.39; N, 8.71
graphic file with name 13065_2020_678_Strh_HTML.gif 5-((E)-4-((E)-(p-tolylimino)methyl)benzylidene)thiazolidine-2,4-dione: m.p. °C: 160–162; Rf value: 0.84a; % yield: 75; IR (KBr pellets) cm−1: 3375.37 (N–H str., thiazolidine ring), 1744.26 (C=O str., thiazolidin-2,4-dione ring), 1695.41 (C=N str., imine group), 1507.28 (C=C str., aromatic ring), 1604.31 (C=C str., methylene group), 3162.34 (C–H str., aromatic ring), 3048.39 (C–H str., aliphatic), 1330.13 (C–N str., thiazolidine ring), 607.48 (C–S bend., thiazolidine ring), 1155.49 (C–C str.); 1H NMR (δ, DMSO): 6.80–8.06 (m, 8H, Ar–H), 7.72 (s, 1H, –CH=), 8.71 (s, 1H, CH=N), 12.32 (s, 1H, NH), 2.33(s, 3H, CH3); M. Formula: C18H14N2O2S; MS: m/z 322.01 (M+); Elemental analysis (CHN) Theoretical calc: C, 67.06; H, 4.38; N, 8.69 Found: C, 67.11; H, 4.39; N, 8.65
graphic file with name 13065_2020_678_Stri_HTML.gif 5-((E)-4-((E)-((2,4-dimethylphenyl)imino)methyl)benzylidene) thiazolidine-2,4-dione: m.p. °C: 134–136; Rf value: 0.81a; % yield: 65; IR (KBr cm−1): 3398.47 (N–H str., thiazolidine ring), 1744.74 (C=O str., thiazolidin-2,4-dione ring), 1699.13 (C=N str., imine group), 1498.40 (C=C str., aromatic ring), 1601.47 (C=C str., methylene group), 3012.68 (C–H str., aromatic ring), 2973.04 (C–H str., aliphatic), 1291.9 (C–N str., thiazolidine ring), 605.41 (C–S bend., thiazolidine ring), 1152.01 (C–C str.); 1H NMR (δ, DMSO): 7.02–8.06 (m, 7H, Ar–H), 7.82 (s, 1H, –CH=), 8.58 (s, 1H, CH=N), 12.12 (s, 1H, NH), 2.28(s, 3H, CH3 o-position), 2.29(s, 3H, CH3 p-position); M. Formula: C19H16N2O2S; MS: m/z 334.99 (M+ − 1); Elemental analysis (CHN) Theoretical calc: C, 67.84; H, 4.79; N, 8.33 Found: C, 67.87; H, 4.79; N, 8.36
graphic file with name 13065_2020_678_Strj_HTML.gif 5-((E)-4-((E)-((2,6-dimethylphenyl)imino)methyl)benzylidene) thiazolidine-2,4-dione: m.p. °C: 100–102; Rf value: 0.73a; % yield: 60; IR (KBr cm−1): 3394.22 (N–H str., thiazolidine ring), 1744.97 (C=O str., thiazolidin-2,4-dione ring), 1702.53 (C=N str., imine group), 1470.88 (C=C str., aromatic ring), 1602.92 (C=C str., methylene group), 3032.72 (C–H str., aromatic ring), 2971.09 (C–H str., aliphatic), 1294.35 (C–N str., thiazolidine ring), 606.56 (C–S bend., thiazolidine ring), 1159.9 (C–C str.); 1H NMR (δ, DMSO): 6.77–8.10 (m, 7H, Ar–H), 7.84 (s, 1H, –CH=), 8.42 (s, 1H, CH=N), 12.32 (s, 1H, NH), 2.08(s, 6H, CH3 o-position); M. Formula: C19H16N2O2S; MS: m/z 334.98 (M+ − 1), 337 (M+ + 1); Elemental analysis (CHN) Theoretical calc: C, 67.84; H, 4.79; N, 8.33 Found: C, 67.85; H, 4.79; N, 8.36
graphic file with name 13065_2020_678_Strk_HTML.gif 5-((E)-4-((E)-((2-fluorophenyl)imino)methyl)benzylidene) thiazolidine-2,4-dione: m.p. °C: 108–110; Rf value: 0.69a; % yield: 75; IR (KBr cm−1): 3429.95 (N–H str., thiazolidine ring), 1745.15 (C=O str., thiazolidin-2,4-dione ring), 1695.31 (C=N str., imine group), 1492.16 (C=C str., aromatic ring), 1604.74 (C=C str., methylene group), 3051.62 (C–H str., aromatic ring), 2979.31 (C–H str., aliphatic), 1323.63 (C–N str., thiazolidine ring), 606.47 (C–S bend., thiazolidine ring), 1158.78 (C–C str.), 1009.17 (C-F bend., o-substitution on phenyl ring); 1H NMR (δ, DMSO): 7.26–7.76 (m, 8H, Ar–H), 7.83 (s, 1H, –CH=), 8.68 (s, 1H, CH=N), 12.51 (s, 1H, NH); M. Formula: C17H11N2O2SF; MS: m/z 327.05 (M+ + 1); Elemental analysis (CHN) Theoretical calc: C, 62.57; H, 3.40; N, 8.58 Found: C, 62.60; H, 3.41; N, 8.60
graphic file with name 13065_2020_678_Strl_HTML.gif 5-((E)-4-((E)-((3-bromophenyl)imino)methyl)benzylidene) thiazolidine-2,4-dione: m.p. °C: 98–100; Rf value: 0.82a; % yield: 80; IR (KBr cm−1): 3437.95 (N–H str., thiazolidine ring), 1744.75 (C=O str., thiazolidin-2,4-dione ring), 1698.27 (C=N str., imine group), 1484.71 (C=C str., aromatic ring), 1606.87 (C=C str., methylene group), 3052.46 (C–H str., aromatic ring), 2976.98 (C–H str., aliphatic), 1328.18 (C–N str., thiazolidine ring), 606.38 (C–S bend., thiazolidine ring), 1161.85 (C–C str.), 637.54 (C–Br bend., p-substitution on phenyl ring); 1H NMR (δ, DMSO): 7.03–8.12 (m, 8H, Ar–H), 7.78 (s, 1H, –CH=), 8.72 (s, 1H, CH=N), 12.64 (s, 1H, NH); M. Formula: C17H11N2O2SBr; Elemental analysis (CHN) Theoretical calc: C, 52.73; H, 2.86; N, 7.23 Found: C, 52.75; H, 2.87; N, 7.23
graphic file with name 13065_2020_678_Strm_HTML.gif 5-((E)-4-((E)-((3-nitrophenyl)imino)methyl)benzylidene)thiazolidine-2,4-dione: m.p. °C: 128–130; Rf value: 0.79a; % yield: 80; IR (KBr cm−1): 3379.48 (N–H str., thiazolidine ring), 1747.82 (C=O str., thiazolidin-2,4-dione ring), 1700.55 (C=N str., imine group), 1522.68 (C=C str., aromatic ring), 1600.01 (C=C str., methylene group), 3034.11 (C–H str., aromatic ring), 2928.16 (C–H str., aliphatic), 1347.29 (C–N str., thiazolidine ring), 606.91 (C–S bend., thiazolidine ring), 1153.91 (C–C str.), 1208.69 (N–O str., m-substitution on phenyl ring), 1413.00 (N=O str., m-substitution on phenyl ring); 1H NMR (δ, DMSO): 7.23–8.09 (m, 8H, Ar–H), 7.77 (s, 1H, –CH=), 8.80 (s, 1H, CH=N), 12.67 (s, 1H, NH); M. Formula: C17H11N3O4S; MS: m/z 352.04 (M+ − 1); Elemental analysis (CHN) Theoretical calc: C, 57.79; H, 3.14; N, 11.89 Found: C, 57.82; H, 3.15; N, 11.91
graphic file with name 13065_2020_678_Strn_HTML.gif 5-((E)-4-((E)-((4-chloro-2-nitrophenyl)imino)methyl)benzylidene) thiazolidine-2,4-dione: m.p. °C: 92–94; Rf value: 0.81a; % yield: 75; IR (KBr cm−1): 3356. 19 (N–H str., thiazolidine ring), 1747.59 (C=O str., thiazolidin-2,4-dione ring), 1700.69 (C=N str., imine group), 1502.15 (C=C str., aromatic ring), 1602.45 (C=C str., methylene group), 3030.51 (C–H str., aromatic ring), 2926.60 (C–H str., aliphatic), 1338.08 (C–N str., thiazolidine ring), 607.48 (C–S bend., thiazolidine ring), 1160.38 (C–C str.), 1249.21 (N–O str., o-substitution on phenyl ring), 1456.19 (N=O str., o-substitution on phenyl ring), 764.11 (C–Cl bend., p-substitution on phenyl ring); 1H NMR (δ, DMSO): 7.03–8.01 (m, 7H, Ar–H), 7.73 (s, 1H, –CH=), 8.03 (s, 1H, CH=N), 12.70 (s, 1H, NH); M. Formula: C17H10N3O4SCl; Elemental analysis (CHN) Theoretical calc: C, 52.65; H, 2.60; N, 10.84 Found: C, 52.67; H, 2.60; N, 10.87
graphic file with name 13065_2020_678_Stro_HTML.gif 5-((E)-4-((E)-((2-methoxyphenyl)imino)methyl)benzylidene) thiazolidine-2,4-dione: m.p. °C: 104–106; Rf value: 0.81a; % yield: 70; IR (KBr cm−1): 3396.28 (N–H str., thiazolidine ring), 1744.31 (C=O str., thiazolidin-2,4-dione ring), 1702.51 (C=N str., imine group), 1504.09 (C=C str., aromatic ring), 1602.96 (C=C str., methylene group), 3050.93 (C–H str., aromatic ring), 2930.71 (C–H str., aliphatic), 1293.57 (C–N str., thiazolidine ring), 606.45 (C–S bend., thiazolidine ring), 1161.16 (C–C str.), 1018.82 (O–CH3 str., o-substitution on phenyl ring); 1H NMR (δ, DMSO): 6.75–7.72 (m, 8H, Ar–H), 7.78 (s, 1H, –CH=), 8.58 (s, 1H, CH=N), 12.61 (s, 1H, NH), 3.77 (s, 3H, OCH3); M. Formula: C18H14N2O3S; MS: m/z 339.12 (M+ + 1); Elemental analysis (CHN) Theoretical calc: C, 63.89; H, 4.17; N, 8.28 Found: C, 63.91; H, 4.17; N, 8.33
graphic file with name 13065_2020_678_Strp_HTML.gif 5-((E)-4-((E)-((3-methoxyphenyl)imino)methyl)benzylidene) thiazolidine-2,4-dione: m.p. °C: 176–178; Rf value: 0.82a; % yield: 65; IR (KBr cm−1): 3380.83 (N–H str., thiazolidine ring), 1742.00 (C=O str., thiazolidin-2,4-dione ring), 1696.51 (C=N str., imine group), 1498.71 (C=C str., aromatic ring), 1601.06 (C=C str., methylene group), 2926.44 (C–H str., aliphatic), 1321.31 (C–N str., thiazolidine ring), 605.30 (C–S bend., thiazolidine ring), 1155.65 (C–C str.), 1029.32 (O–CH3 str., m-substitution on phenyl ring); 1H NMR (δ, DMSO): 6.58–8.05 (m, 8H, Ar–H), 7.73 (s, 1H, –CH=), 8.68 (s, 1H, CH=N), 12.32 (s, 1H, NH), 3.85(s, 3H, OCH3); M. Formula: C18H14N2O3S; MS: m/z 338.8 (M+ + 1); Elemental analysis (CHN) Theoretical calc: C, 63.89; H, 4.17; N, 8.28 Found: C, 63.92; H, 4.17; N, 8.31
graphic file with name 13065_2020_678_Strq_HTML.gif 5-((E)-4-((E)-((4-methoxyphenyl)imino)methyl)benzylidene) thiazolidine-2,4-dione: m.p. °C: 130–132; Rf value: 0.77a; % yield: 75; IR (KBr cm−1): 3444.26 (N–H str., thiazolidine ring), 1743.88 (C=O str., thiazolidin-2,4-dione ring), 1702.79 (C=N str., imine group), 1505.14 (C=C str., aromatic ring), 1614.33 (C=C str., methylene group), 3065.92 (C–H str., aromatic ring), 2926.15 (C–H str., aliphatic), 1291.79 (C–N str., thiazolidine ring), 606.22 (C–S bend., thiazolidine ring), 1155.22 (C–C str.), 1024.26 (O–CH3 str., o-substitution on phenyl ring); 1H NMR (δ, DMSO): 6.98–8.04 (m, 8H, Ar–H), 7.78 (s, 1H, –CH=), 8.71 (s, 1H, CH=N), 12.42 (s, 1H, NH), 3.78(s, 3H, OCH3); M. Formula: C18H14N2O3S; MS: m/z 338.98 (M+ + 1); Elemental analysis (CHN) Theoretical calc: C, 63.89; H, 4.17; N, 8.28 Found: C, 63.93; H, 4.17; N, 8.30
graphic file with name 13065_2020_678_Strr_HTML.gif 5-((E)-4-((E)-((4-fluorophenyl)imino)methyl)benzylidene) thiazolidine-2,4-dione: m.p. °C: 104–106; Rf value: 0.83a; % yield: 70; IR (KBr cm−1): 3431.86 (N–H str., thiazolidine ring), 1743.59 (C=O str., thiazolidin-2,4-dione ring), 1697.01 (C=N str., imine group), 1501.17 (C=C str., aromatic ring), 1612.03 (C=C str., methylene group), 3039.20 (C–H str., aromatic ring), 2925.63 (C–H str., aliphatic), 1292.50 (C–N str., thiazolidine ring), 604.82 (C–S bend., thiazolidine ring), 1152.02 (C–C str.), 1012.73 (C-F str., p-substitution on phenyl ring); 1H NMR (δ, DMSO): 6.77–7.78 (m, 8H, Ar–H), 7.77 (s, 1H, –CH=), 7.87 (s, 1H, CH=N), 12.60 (s, 1H, NH); M. Formula: C17H11N2O2SF; MS: m/z 324.85 (M+ − 1); Elemental analysis (CHN) Theoretical calc: C, 62.57; H, 3.40; N, 8.58 Found: C, 62.58; H, 3.40; N, 8.59
graphic file with name 13065_2020_678_Strs_HTML.gif 5-((E)-4-((E)-((4-nitrophenyl)imino)methyl)benzylidene)thiazolidine-2,4-dione: m.p. °C: 118–120; Rf value: 0.83a; % yield: 75; IR (KBr cm−1): 3369.56 (N–H str., thiazolidine ring), 1743.23 (C=O str., thiazolidin-2,4-dione ring), 1698.03 (C=N str., imine group), 1503.33 (C=C str., aromatic ring), 1601.16 (C=C str., methylene group), 3052.03 (C–H str., aromatic ring), 2925.51 (C–H str., aliphatic), 1310.97 (C–N str., thiazolidine ring), 608.61 (C–S bend., thiazolidine ring), 1163.00 (C–C str.), 1212.91 (N–O str., p-substitution on phenyl ring), 1412.67 (N=O str., p-substitution on phenyl ring); 1H NMR (δ, DMSO): 6.60–8.28 (m, 8H, Ar–H), 7.78 (s, 1H, –CH=), 8.72 (s, 1H, CH=N), 12.62 (s, 1H, NH); M. Formula: C17H11N3O4S; Elemental analysis (CHN) Theoretical calc: C, 57.79; H, 3.14; N, 11.89 Found: C, 57.80; H, 3.14; N, 11.88
graphic file with name 13065_2020_678_Strt_HTML.gif 5-((E)-4-((E)-(dodecylimino)methyl)benzylidene)thiazolidine-2,4-dione: m.p. °C: 106–108; Rf value: 0.43a; % yield: 60; IR (KBr cm−1): 3339.52 (N–H str., thiazolidine ring), 1699.02 (C=O str., thiazolidin-2,4-dione ring), 1608.43 (C=N str., imine group), 1461.90 (C=C str., aromatic ring), 1562.34 (C=C str., methylene group), 3047.23 (C–H str., aromatic ring), 2923.03 (C–H str., aliphatic), 1296.98 (C–N str., thiazolidine ring), 608.00 (C–S bend., thiazolidine ring), 1165.06 (C–C str.); 1H NMR (δ, DMSO): 7.28–7.98 (m, 4H, Ar–H), 7.78 (s, 1H, –CH=), 8.35 (s, 1H, CH=N), 12.62 (s, 1H, NH), 1.23–1.69 (m, 20H, CH2), 0.84 (t, J = 9.00 Hz, 3H, CH3), 3.66 (m, 2H, CH2 adjacent to CH=N); M. Formula: C23H32N2O2S; MS: m/z 401.12 (M+ + 1), 399.09 (M+ − 1); Elemental analysis (CHN) Theoretical calc: C, 68.96; H, 8.05; N, 6.99 Found: C, 68.97; H, 8.05; N, 6.98

TLC mobile phase = a Chloroform:Methanol: 9:1

bChloroform:Toluene:GAA: 1:1:0.1

cEthyl Acetate

dMethanol:Toluene:GAA: 1:1:0.1