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S. Begum et al.
93 (70), 77 (49.9) 1H-NMR (400 MHz, CDCl3); ꢁ 8.1 (2H, s, 2 N–H), 7.46 (1H, d,
J ¼ 7.8 Hz, H-6), 7.44 (2H, d, J ¼ 7.54 Hz, H-20,60), 7.39 (1H, m, H-40), 7.36 (1H, d,
J ¼ 6.6 Hz, H-3), 7.32 (1H, dd, J ¼ 8.4, 8.9 Hz, H-4), 7.28 (1H, dd, J ¼ 7.7, 7.6 Hz, H-5),
7.15 (2H, m, H-30,50),1.55 (1H, broad s, SH).
N-(p-Bromophenyl)-N0-phenylthiourea (9). C13H11N2BrS (Calcd: 307.9900; found:
307.9805), yield 77.8%, m.p. 148ꢀC (sharp) (lit. 148ꢀC) (Furniss et al., 1986; Otterbacher
& Whitemore, 1929), pale yellow crystalline solid; IR (KBr), ꢀmax (cmꢁ1): 3433.1 and
3209.3 (N–H stretching), 2927.7, 2806.2, 1591.2, 1542.9, 1332.7 (N–H amide), 1292.2,
1238.2 (C¼S), 1064.6, 1010.6, 925.8; EIMS m/z (rel. int.%): 307.8 [Mþ] (26.8), 271.9 (9.97),
1
170.8 (100), 93.0 (90.58), 76.9 (53.0) H-NMR (400 MHz, CDCl3); ꢁ 8.2 (2H, s, NH),
7.46 (5H, m, C6H5), 7.32 (2H, d, J ¼ 7.2 Hz, H-3,5), 7.27 (2H, d, J ¼ 7.32 Hz, H-2,6), 1.72
(1H, s, SH).
N-Phenyl-N0-(2-pyridinyl)thiourea (10). C12H11N3S (Calcd: 229.0675; found: 229.0684),
yield 75.9%, m.p. 171–172ꢀC (Lit. 172ꢀC) (Sarkis & Faisal, 1985), white shiny crystalline
solid; IR (KBr), ꢀmax (cmꢁ1): 3462.3 and 3220.2 (N–H stretching), 1601.1, 1598.1, 1537.9,
1473.6, 1431.5, 1353.9, 1342.2 (N–H amide), 1265.1, 1184.8 and 1142.4 (C¼S),; EIMS m/z
(rel. int.%): 229.0 (71.43) [Mþ], 196.1 (27.13), 137.0 (36.29), 94.0 (100), 78.0 (50.47);
1H-NMR (400 MHz, CDCl3); ꢁ 13.68 (1H, s, N–H), 9.39 (1H, s, N0–H), 8.19 (1H, d,
J ¼ 4.25 Hz, H-6), 7.65 (2H, d, J ¼ 7.86 Hz, H-20,60), 7.62 (1H, m, H-4), 7.39 (2H, dd,
J ¼ 7.6, 7.8 Hz, H-30,50), 7.24 (1H, dd, J ¼ 7.4, 7.3 Hz, H-40), 6.97 (2H, d, J ¼ 6.92 Hz, H-3),
6.94 (1H, m, H-5), 1.67 (1H, s, SH).
N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-N0-phenylthiourea
(11).
C18H18N4OS (Calcd: 338.1203; HRFAB-MS 339.1290 (339.1281 for C18H19N4OS), yield
98.9%, m.p. 198ꢀC (sharp) (lit. 198ꢀC) (Cuhna et al., 2005) crystalline solid; IR (KBr),
ꢀmax (cmꢁ1): 3441.4 and 3272.9 (N–H stretching), 3034.3 (Ar–H stretching), 1632.8,
1600.3, 1585.9, 1532.6, 1494.8, 1450.7, 1416.3, 1313.5 (N–H amide), 1293.1S (C¼S); EIMS
m/z (rel. int.%): 304 (15.1) [Mþ ꢁ H2S], 244.96 (100) [Mþ ꢁ NH – C6H5], 203 (46.8)
[Mþ ꢁ CSNHC6H5], 134.97 (64.2) [CSNHC6H5], 93.1 (43.1) [NHC6H5], 77.0 (38.5) [C6H5];
positive ion FAB-MS m/z: [M þ H]þ, 339.1, HRFAB-MS m/z: 339.1290 (Calcd: 339.1281
1
for C18H19N4OS); H-NMR (400 MHz, DMSO-d6); ꢁ 9.7 (2H, broad s, NH), 7.51 (4H, d,
J ¼ 7.6 Hz, H-20,200, 60,600), 7.45 (1H, m, H-40), 7.33 (4H, dd, J ¼ 7.73, 8.85 Hz,
H-30,300,50,500), 7.13 (1H, m, H-400), 3.1 (3H, s, N–CH3), 2.4 (3H, s, C–CH3), 2.18 (1H,
13
broad s, SH); C-NMR (CDCl3): 181.45 (C-8), 161.72 (C-3), 153.05 (C-10), 139.7 (C-100),
134.94 (C-5), 129.18 (C-30,C-50), 128.32 (C-300,C-500), 126.6 (C-20,C-60), 124.818 (C-40,400),
124.04 (C-200,C-600), 113.4 (C-4), 35.59 (C-6), 10.90 (C-7).
N-(1-Naphthyl)-N0-phenylthiourea (12). C17H14N2S (Calcd: 278.0879; found: 277.9988),
yield 88.6%, m.p. 196ꢀC (sharp) (Lit. 165ꢀC) (Furniss et al., 1986), white crystalline solid;
IR (KBr), ꢀmax (cmꢁ1): 3450.76 (N–H stretching), 1627.91, 1594.28 1526.50, 1493.43,
1435.97, 1393.9, 1329.17 (N–H amide), 1274.1, 1218.7 (C¼S); EIMS m/z (rel. int.%):
278 (2.9) [Mþ], 244 (39.7) [Mþ ꢁ H2S], 185 (82.6)[Mþ ꢁ C6H5NH], 143 (68.6)
1
[Mþ ꢁ C6H5NHCS], 127 (33.4) Naphthyl group; H-NMR (400 MHz, DMSO-d6); ꢁ 9.79
(2H, broad s, NH), 8.00 (2H, d, J ¼ 7.2 Hz, H-4, 5), 7.96 (2H, d, J ¼ 7.5 Hz, H-20, 60), 7.84
(2H, d, J ¼ 7.2 Hz, H-30, 50), 7.54 (6H, m, H-3, 4, 40 6, 7, 8), 2.4 (1H, broad s, SH).
2-Phenyl-N-phenyl-1-hydrazinecarbothioamide (13). C13H13N3S (Calcd: 243.0832; found:
243.0802), yield 55.5%, m.p. 171–172ꢀC (lit. 172ꢀC) (Furniss et al., 1986), crystalline solid;