ACCEPTED MANUSCRIPT
100%], 387[M+.+2, 14.28 %] Anal.Calcd. for C19H19N3O2S2: C, 59.20; H, 4.97; N,
10.90, Found: C, 59.01; H, 4.63; N, 10.85%.
(E)-1-(1-(4-Methyl-2-phenylthiazol-5-yl)ethylidene)-2-(4-sulfamoyl-phenyl)
hydrazine (9b).
o
Yellow powder; Yield: 84%; mp: 275-277 C; IR (KBr, cm-1): 3382, 3300 (NH,
NH2), 3184 (C-H aromatic), 2936 (C-H aliphatic), 1592 (C=N), 1342, 1156 (SO2);
1H-NMR (DMSO-d6); δ 2.38 (s, 3H, CH3), 2.66 (s, 3H, CH3-C=N), 7.11(s, 2H, NH2)
7.28 (d, 2H, J = 8.4 Hz, H-2, H-6 of sulfamoylphenyl), 7.50 ( 3H, phenyl H-3, H-4,
H-5), 7.67 (d, 2H, J = 8.4 Hz, sulfamoylphenyl H-3, H-5), 7.94 (m, 2H, phenyl H-2,
H-6), 9.90 (s, 1H, NH (D2O exchangeable). 13C NMR (DEPTQ); 16.98 (CH3,
thiazole), 18.75 (CH3-C=N), 112.78 (C-2, C-6 sulfamoylphenyl), 126,34 (C3, C5 of
sulfamoyl phenyl), 129.20 (C3, C5 of phenyl), 129.70 (C-2, C-6 of phenyl), 130.66
(C-4 of phenyl), 133.35 (C-1of sulfamoylphenyl), 133.54 (C=NH-), 134.43 (C-1 of
phenyl), 138.95 (C-4 of sulfamoyl phenyl), 148.46 (C-5 of thiazole), 149.86 (C-4 of
thiazole), 163.40 (C-2 of thiazole); 386 [(M)+., 100%]. Anal. Calcd. for
C18H18N4O2S2 : C, 55.94; H, 4.69; N, 14.50; Found: C, 56.01; H, 4.63; N, 14.25%.
4.1.5. Synthesis 5-(4-Methyl-2-phenylthiazol-5-yl)-1-(4-(N,N-dimethylformamidine-
sulfam oyl) phenyl) - 1H-pyrazole (10).
A solution of 9b (0.38 g, 0.001mol) and DMFDMA (0.03 mol) in toluene (30 mL)
was heated under reflux for 24 h., (monitored by TLC). The reaction mixture is
evaporated solid separated , dried then separated by preparative T.L.C as 10 as Off
white powder ; Yield: 39 %; mp: 175-177 oC; IR (KBr, cm-1): 2990 (C-H aromatic),
2933 (C-H aliphatic), 1590 (C=N), 1344, 1133 (SO2); 1H NMR (DMSO-d6); δ 2.15
(s, 3H, thiazole CH3), 2.90 (s, 3H, =N-CH3), 3.1(s, 3H, =NCH3), 6.84(d, 1H, J = 2.0
Hz, pyrazole H-4), 7.49-7.53 (m, 5H, phenyl H-3, H4, H5 and H2, H-6 of
sulfomylphenyl H-2, H-6), 7.82 (d, 2H, J = 8.8 Hz, sulfamoylphenyl H-5, H-3),
7.87-7.90 (m, 2H, phenyl H-2, H-6), 7.93 (d, 1H, J = 2.0 Hz, pyrazole H-5), 8.21 (s,
1H, olfenic H); 13C NMR (DEPTQ); 16.24 (thiazole CH3), 35.59 (=NCH3), 40.48
(=NCH3 ), 111.95( C-4 pyrazole), 118.91 (C-1 of sulfamoylphenyl), 124.99 (C3, C5
phenyl), 126.51 (C2, C6 of phenyl), 127.65 (C-2, C-6 sulfamoylphenyl), 129.82 (C-3,
C-5 sulfamoylphenyl), 131.25 (C-5 of phenyl), 132.51(C-1 of phenyl), 139.12 (C-4 of
ulfamoylphenyl), 141.81(C-3 of pyrazole), 141.86(C-5 of pyrazole), 142.48(C-5 of
thiazole), 152.98(C-4 of thiazole), 160.37 (olfenic CH), 168.74 (C-2 of thiazole). (
17