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7.69–7.58 (m, 2H), 7.30–7.15 (m, 2H), 4.92 (d, J ¼ 4.0 Hz, 2H), 150.7, 51.9, 42.6, 32.2, 31.3, 31.1, 30.3, 26.7, 26.1, 22.4, 22.2,
3.88–3.70 (m, 8H); 13C NMR (CDCl3, 100 MHz) d (ppm) 181.8, 13.8, 13.7; IR (neat, cmꢁ1) 2912, 1720, 1635, 1272, 1201, 692;
156.1, 148.5, 137.1, 122.6, 122.4, 66.3, 50.2, 47.7; IR (neat, cmꢁ1
)
HRMS (EI, m/z) calcd for C15H28N2OS (M+) 284.1922, found
3320, 2961, 2923, 2857, 1594, 1570, 1535, 1476, 1436, 1330, 284.1925.
1
1274, 1208, 1116, 1027, 890, 759; HRMS (EI, m/z) calcd for
11H15N3OS (M+) 237.0936, found 237.0933.
(Z)-3-Benzyl-2-(benzylimino)thiazolidin-4-one (5b). H NMR
(CDCl3, 400 MHz) d (ppm) 7.39–7.35 (m, 2H), 7.28–7.15 (m, 8H),
C
N-Phenylmorpholine-4-carbothioamide (3d). 1H NMR 4.88 (s, 2H), 4.44 (s, 2H), 3.78 (s, 2H); 13C NMR (CDCl3, 100 MHz)
(CDCl3, 400 MHz) d (ppm) 7.40–7.28 (m, 3H), 7.16–7.09 (m, 3H), d (ppm) 171.4, 152.6, 139.2, 136.1, 129.0, 128.9, 128.7, 128.5,
3.90–3.60 (m, 8H); 13C NMR (CDCl3, 100 MHz) d (ppm) 183.5, 128.3, 128.3, 128.1, 127.7, 127.3, 126.8, 55.3, 46.0, 32.7; IR (neat,
139.9, 129.1, 125.3, 123.2, 66.1, 49.5; IR (neat, cmꢁ1) 3204, 3034, cmꢁ1) 3052, 1720, 1635, 1590, 1495, 1374, 1272, 1201, 690;
2962, 2921, 2855, 1595, 1528, 1497, 1448, 1335, 1308, 1228, HRMS (EI, m/z) calcd for C17H16N2OS (M+) 296.0983, found
1209, 1113, 1030, 703; HRMS (EI, m/z) calcd for C11H14N2OS 296.0987.
(M+) 222.0827, found 222.0831.
(Z)-3-Phenyl-2-(phenylimino)thiazolidin-4-one (5d). 1H NMR
1,3-Dihexylthiourea (4a). 1H NMR (CDCl3, 400 MHz) d (ppm) (CDCl3, 400 MHz) d (ppm) 7.48–6.82 (m, 10H), 3.92 (s, 2H); 13
C
5.72 (brs, 2H), 3.35 (brs, 4H), 1.65–1.53 (m, 4H), 1.34–1.23 (m, NMR (CDCl3, 100 MHz) d (ppm) 171.4, 154.9, 148.0, 134.7, 129.4,
12H), 0.86 (t, 6H, J ¼ 6.6 Hz); 13C NMR (CDCl3, 100 MHz) d 129.1, 129.0, 128.0, 124.6, 120.9, 32.9; IR (neat, cmꢁ1) 3048,
(ppm) 180.8, 44.1, 31.1, 28.7, 26.2, 22.1, 13.5; IR (neat, cmꢁ1
)
2936, 1727, 1635, 1580, 1455, 1374, 1269, 1195, 693; HRMS (EI,
3320, 3069, 2930, 2861, 1557, 1334, 1240, 1118, 997, 878, 845, m/z) calcd for C15H12N2OS (M+) 268.0670, found 268.0673.
726; HRMS (EI, m/z) calcd for C13H28N2S (M+) 244.1973, found
244.1976.
(E)-2-(p-Tolylimino)-3-p-tolylthiazolidin-4-one (5e). 1H NMR
(CDCl3, 400 MHz) d (ppm) 7.25 (d, J ¼ 8.4 Hz, 2H), 7.19 (d, J ¼
1,3-Dibenzylthiourea (4b). 1H NMR (CDCl3, 400 MHz) d 8.4 Hz, 2H), 7.04 (d, J ¼ 8.4 Hz, 2H), 6.73 (d, J ¼ 8.4 Hz, 2H), 3.89
(ppm) 7.33–7.20 (m, 10H), 6.06 (brs, 2H), 4.60 (brs, 4H); 13C (s, 2H), 2.32 (s, 3H), 2.24 (s, 3H); 13C NMR (CDCl3, 100 MHz) d
NMR (CDCl3, 100 MHz) d (ppm) 182.0, 136.7, 128.9, 127.9, 127.5, (ppm) 171.6, 154.8, 145.6, 139.0, 134.1, 132.1, 130.1, 129.7,
48.5; IR (neat, cmꢁ1) 3324, 2972, 2912, 2876, 1645, 1634, 1557, 127.7, 120.7, 32.8, 21.3, 20.9; IR (neat, cmꢁ1) 3051, 2919, 1722,
1451, 1315, 943, 807, 770; HRMS (EI, m/z) calcd for C15H16N2S 1638, 1591, 1581, 1487, 1370, 1284, 1203, 1132, 693; HRMS (EI,
(M+) 256.1034, found 256.1036.
m/z) calcd for C17H16N2OS (M+) 296.0983, found 296.0979.
(E)-2-(4-Ethoxyphenylimino)-3-(4-ethoxyphenyl)thiazolidin-
1,3-Diphenylthiourea (4d). 1H NMR (CDCl3, 400 MHz) d
(ppm) 8.02–7.82 (brs, 2H), 7.42–7.34 (m, 8H), 7.28–7.24 (m, 2H); 4-one (5f). 1H NMR (CDCl3, 400 MHz) d (ppm) 7.20 (d, J ¼ 8.4 Hz,
13C NMR (CDCl3, 100 MHz) d (ppm) 179.9, 137.0, 129.6, 127.1, 2H), 6.93 (d, J ¼ 8.4 Hz, 2H), 6.77 (s, 4H), 3.98 (q, J ¼ 7.2 Hz, 2H),
125.3; IR (neat, cmꢁ1) 3607, 3211, 3035, 3025, 2876, 1633, 1600, 3.93 (q, J ¼ 7.2 Hz, 2H), 3.88 (s, 2H), 1.34 (t, J ¼ 7.2 Hz, 3H), 1.33
1556, 1451, 1344, 1315, 1242, 1071, 933, 696; HRMS (EI, m/z) (t, J ¼ 7.2 Hz, 3H); 13C NMR (CDCl3, 100 MHz) d (ppm) 171.7,
calcd for C13H12N2S (M+) 228.0721, found 228.0719.
159.1, 156.1, 155.0, 141.2, 129.0, 127.1, 121.9, 115.2, 114.9, 63.6,
1,3-Di-p-tolylthiourea (4e). 1H NMR (CDCl3, 400 MHz) d 63.5, 32.7, 14.9, 14.8; IR (neat, cmꢁ1) 3421, 2983, 1728, 1633,
(ppm) 7.95 (brs, 2H), 7.16 (d, J ¼ 8.4 Hz, 4H), 7.10 (d, J ¼ 8.4 Hz, 1508, 1477, 1393, 1246, 1194, 1045, 837, 789; HRMS (EI, m/z)
4H), 2.26 (s, 6H); 13C NMR (CDCl3, 100 MHz) d (ppm) 180.0, calcd for C19H20N2O3S (M+) 356.1195, found 356.1198.
136.9, 134.5, 130.0, 125.4, 21.0; IR (neat, cmꢁ1) 3605, 3212, 3035,
(E)-2-(4-Iodophenylimino)-3-(4-iodophenyl)thiazolidin-4-one
3024, 1633, 1601, 1555, 1451, 1315, 1242, 1071, 938, 876, 845, (5g). 1H NMR (CDCl3, 400 MHz) d (ppm) 7.83 (d, J ¼ 8.4 Hz, 2H),
720; HRMS (EI, m/z) calcd for C15H16N2S (M+) 256.1034, found 7.60 (d, J ¼ 8.4 Hz, 2H), 7.10 (d, J ¼ 8.4 Hz, 2H), 7.65 (d, J ¼ 8.4
256.1031.
Hz, 2H), 3.98 (s, 2H); 13C NMR (CDCl3, 100 MHz) d (ppm) 170.9,
1,3-Bis(4-ethoxyphenyl)thiourea (4f). 1H NMR (CDCl3, 400 155.1, 147.4, 138.6, 138.2, 134.2, 129.7, 123.0, 94.9, 88.7, 32.9; IR
MHz) d (ppm) 7.58 (brs, 2H), 7.18 (dd, J ¼ 8.8, 3.2 Hz, 4H), 6.83 (neat, cmꢁ1) 3046, 2943, 2926, 2854, 1728, 1628, 1483, 1366,
(d, J ¼ 8.8 Hz, 4H), 3.95 (q, J ¼ 7.2 Hz, 4H), 1.34 (t, J ¼ 7.2 Hz, 1273, 1191, 1150, 1057, 874, 828, 808, 736; HRMS (EI, m/z) calcd
6H); 13C NMR (CDCl3, 100 MHz) d (ppm) 181.0, 158.0, 127.5, for C15H10I2N2OS (M+) 519.8603, found 519.8600.
115.2, 63.7, 14.7; IR (neat, cmꢁ1) 3214, 3025, 2975, 2911, 2876,
1578, 1554, 1535, 1512, 1360, 1339, 1299, 1245, 1222, 1171,
Acknowledgements
1116, 1051, 835, 817, 724; HRMS (EI, m/z) calcd for C17H20N2O2S
(M+) 316.1245, found 316.1241.
We acknowledge the National Science Council of the Republic
1,3-Bis(4-iodophenyl)thiourea (4g). 1H NMR (CDCl3, 400 of China and CEM Corporation for nancial and instrument
MHz) d (ppm) 8.25 (brs, 2H), 7.68 (d, J ¼ 8.8 Hz, 4H), 7.23 (d, J ¼ support. (NSC 100-2113-M-040-006, NSC 99-2113-M-040-003-
8.8 Hz, 4H); 13C NMR (CDCl3, 100 MHz) d (ppm) 180.7, 139.5, MY2).
137.3, 125.6, 88.5; IR (neat, cmꢁ1) 3211, 3032, 3024, 2910, 2869,
1633, 1603, 1555, 1450, 1313, 1241, 1071, 934, 870; HRMS (EI,
Notes and references
m/z) calcd for C13H10I2N2S (M+) 479.8654, found 479.8658.
(E)-3-Hexyl-2-(hexylimino)thiazolidin-4-one (5a). 1H NMR
(CDCl3, 400 MHz) d (ppm) 3.75 (s, 2H), 3.67 (t, J ¼ 7.4 Hz, 2H),
3.24 (d, J ¼ 6.8 Hz, 2H), 1.64–1.52 (m, 6H), 1.38–1.22 (m, 10H),
0.90–0.80 (m, 6H); 13C NMR (CDCl3, 100 MHz) d (ppm) 171.2,
1 A. Ranise, A. Spallarossa, O. Bruno, S. Schenone, P. Fossa,
G. Menozzi, F. Bondavalli, L. Mosti, A. Capuano,
F. Mazzeo, G. Falcone and W. Filippelli, Il Farmaco., 2003,
58, 765.
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RSC Adv., 2014, 4, 1276–1282 | 1281