3.1.2.1 N-(5-(2-((4-chlorophenyl)amino)-2-oxoethyl)-4-oxo-3-phenyl-2-thioxoimid -azolidin-1-yl)-4-methylbenzamide (7e)
Yield 55 %; white solid; mp.= 269–270 ºC; 1H NMR (500 MHz, DMSO-d6) δ 11.37 (s, 1H, Hd), 10.31 (s, 1H, He), 7.84 (d, J = 8.2 Hz, 2H, H-Ar), 7.64–7.30 (m, 12H, H-Ar), 4.89 (t, J = 3.8 Hz, 1H, Hc), 3.22–3.08 (m, 2H, Ha, Hb), 2.37 (s, 3H, CH3); 13C NMR (125 MHz, DMSO-d6) δ 184.49 (C1 = S), 172.00 (C4 = O), 167.35 (C2 = O), 165.95 (C3 = O), 143.13, 138.32, 134.35, 129.55, 129.46, 129.32, 129.15, 128.96, 128.24, 127.32, 121.10 (C-Ar), 60.17 (CHc), 35.43 (CHaHb), 21.55 (CH3); IR (KBr, cm− 1): 3305 (NH amide), 3219 (Ph-NH), 3064 (CH-arom.), 2995 (CH-aliph.),1753 (C = O asym.),1664 (C = O sym.),1602(C = O amide),1539, 1494 (C = C arom.), 1433 (C = S), 1330 (C-N); MS (m/z): 492 [M]+.
3.1.2..2 N-(5-(2-((4-bromophenyl)amino)-2-oxoethyl)-4-oxo-3-phenyl-2-thioxo imi d-azolidin-1-yl)-4-methylbenzamide (7f)
Yield 90 %; white solid; mp.= 262–263 ºC; 1H NMR (500 MHz, DMSO-d6) δ 11.37 (s, 1H,Hd), 10.32 (s, 1H, He), 7.84 (d, J = 7.9 Hz, 2H, H-Ar), 7.58–7.54 (m, 4H), 7.53–7.48 (m, 3H, H-Ar), 7.41 (d, J = 7.8 Hz, 2H, H-Ar), 7.33 (d, J = 7.9 Hz, 2H, H-Ar), 4.90 (s, 1H, Hc), 3.19–3.15 (m, 2H, Ha, Hb), 2.38 (s, 3H, CH3); 13C NMR (125 MHz, DMSO-d6) δ 184.48 (C1 = S), 171.99 (C4 = O), 167.37 (C2 = O), 165.94 (C3 = O), 143.12, 138.72, 134.33, 132.05, 129.55, 129.46, 129.32, 129.11, 128.95, 128.23, 121.48, 115.34 (C-Ar), 60.16 (CHc), 35.45 (CHaHb), 21.55 (CH3); IR (KBr, cm− 1): 3273 (NH amide), 3182 (Ph-NH), 3047 (CH-arom.), 2993 (CH-aliph.),1753 (C = O asym.),1666 (C = O sym.),1610(C = O amide),1531, 1489 (C = C arom.), 1436 (C = S), 1330 (C-N); MS (m/z): 538 [M + H]+.
3.1.2.3 4-Methyl-N-(4-oxo-5-(2-oxo-2-(p-tolylamino)ethyl)-3-phenyl-2-thioxoimid azoli din-1-yl)benzamide (7g)
Yield 73 %, white solid; mp.= 250–251 ºC; 1H NMR (500 MHz, DMSO-d6) δ 11.41 (s, 1H, Hd), 10.09 (s, 1H, He), 7.86 (d, J = 7.9 Hz, 2H, H-Ar), 7.57–7.29 (m, 9H, H-Ar), 7.12 (d, J = 8.1 Hz, 2H, H-Ar), 4.89 (t, J = 3.9 Hz, 1H, Hc), 3.2–3.08 (m, 2H, Ha, Hb), 2.37 (s, 3H, CH3), 2.25 (s, 3H, CH3); 13C NMR (125 MHz, DMSO-d6) δ 184.57 (C1 = S), 172.11 (C4 = O), 166.88 (C2 = O), 165.96 (C3 = O), 143.11, 136.91, 134.41, 132.65, 129.58, 129.55, 129.44, 129.29, 129.16, 128.99, 128.26, 119.56 (C-Ar), 60.24 (CHc), 35.38 (CHaHb), 21.56 (CH3), 20.93 (CH3); IR (KBr, cm− 1): 3305 (NH amide), 3221 (Ph-NH), 3035 (CH-arom.), 2997 (CH-aliph.),1755 (C = O asym.),1666 (C = O sym.),1610 (C = O amide),1539, 1498 (C = C arom.), 1433 (C = S), 1330 (C-N); MS (m/z): 472 [M]+.
3.1.2.4 4-Methyl-N-(4-oxo-5-(2-oxo-2-(phenylamino)ethyl)-3-phenyl-2-thioxoimid azolid in-1-yl) benzamide (7h)
Yield 90 %; white solid; mp.= 268–269 ºC; 1H NMR (500 MHz, DMSO-d6) δ 11.40 (s, 1H, Hd), 10.17 (s, 1H, He), 7.85 (d, J = 7.8 Hz, 2H, H-Ar), 7.60–7.03 (m, 12H, H-Ar), 4.93–4.85 (m, 1H, Hc), 3.21–3.13 (m, 2H, Ha, Hb), 2.37 (s, 3H, CH3); 13C NMR (125 MHz, DMSO-d6) δ 184.52 (C1 = S), 172.08 (C4 = O), 167.14 (C2 = O), 165.96 (C3 = O), 143.11, 139.39, 134.39, 129.55, 129.45, 129.30, 129.21, 128.98, 128.25, 123.76, 119.54 (C-Ar), 60.21 (CHc), 35.43 (CHaHb), 21.55 (CH3); IR (KBr, cm− 1): 3319 (NH amide), 3221 (Ph-NH), 3059 (CH-arom.), 2912 (CH-aliph.),1753 (C = O asym.),1668 (C = O sym.),1600 (C = O amide),1546, 1498 (C = C arom.), 1438 (C = S), 1327 (C-N); MS (m/z): 458 [M]+.