formula: C18H16ClN3O2S; Mol. Wt.: 373; IR (KBr, vmax/cm-1): 3347 (N-H), 3095 (Ar C-H), 1683 (C=N), 1642 (C=O), 1590 (Ar C=C), 1270 (C-O-C), 680 (C-Cl), 623 (C-S); 1H-NMR (400 MHz, CDCl3, d/ppm): 8.73 (s, 1H, CONH), 7.92 (d, J = 8.0 Hz, 1H, H-6'), 7.56 (d, J = 8.0 Hz, 1H, H-3'), 7.54 (d, J = 7.6 Hz, 1H, H-6'''), 7.49 (t, J = 7.6 Hz, 1H, H-5'), 7.41 (t, J = 7.6 Hz, 1H, H-4'), 7.07 (t, J = 7.6 Hz, 1H, H-5'''), 6.97 (d, J = 7.6 Hz, 1H, H-4'''), 4.06 (s, 2H, H-2''), 2.32 (s, 3H, CH3-2'''), 2.14 (s, 3H, CH3-3'''); EIMS (m/z): 375 [M+2]+, 373 [M]+, 253 [C10H6ClN2O2S]+, 225 [C9H6ClN2OS]+, 212 [C8H5ClN2OS] , 193 [C10H11NOS] , 179 [C8H4ClN2O]+, 153 [C7H4ClNO]+, 148 [C9H10NO]+, 139 [C7H4ClO]+, 137 [C7H4ClN]+, 121 [C8H11N]+, 111 [C6H4Cl]+, 105 [C8H9]+.
formula: C18H16ClN3O2S; Mol. Wt.: 373; IR (KBr, vmax/cm-1): 3326 (N-H), 3077 (Ar C-H), 1663 (C=N), 1643 (C=O), 1592 (Ar C=C), 1222 (C-O-C), 684 (C-Cl), 630 (C-S); 1H-NMR (400 MHz, CDCl3, d/ppm): 8.73 (s, 1H, CONH), 7.90 (d, J = 7.6 Hz, 1H, H-6'), 7.68 (d, J = 7.6 Hz, 1H, H-6'''), 7.55 (d, J = 8.0 Hz, 1H, H-3'), 7.48 (t, J = 7.6 Hz, 1H, H-5'), 7.41 (t, J = 7.6 Hz, 1H, H-4'), 6.99 (d, J = 7.6 Hz, 1H, H-5'''), 6.96 (s, 1H, H-3'''), 4.06 (s, 2H, H- 2''), 2.25 (s, 3H, CH3-2'''), 2.22 (s, 3H, CH3-4'''); EIMS (m/z): 375 [M+2]+, 373 [M]+, 253 [C10H6ClN2O2S]+, 225 [C9H6ClN2OS]+, 212 [C8H5ClN2OS]+, 193 [C10H11NOS]+, 179 [C8H4ClN2O]+, 153 [C7H4ClNO]+, 148 [C9H10NO]+, 139 [C7H4ClO]+, 137 [C7H4ClN]+, 121 [C8H11N]+, 111 [C6H4Cl]+, 105 [C8H9]+.
formula: C18H16ClN3O2S; Mol. Wt.: 373; IR (KBr, vmax/cm-1): 3293 (N-H), 3069 (Ar C-H), 1669 (C=N), 1650 (C=O), 1599 (Ar C=C), 1197 (C-O-C), 680 (C-Cl), 623 (C-S); 1H-NMR (400 MHz, CDCl3, d/ppm): 8.73 (s, 1H, CONH), 7.90 (dd, J = 7.6, 2.4 Hz, 1H, H-6'), 7.53 (d, J = 8.0 Hz, 1H, H- 3'), 7.48 (dt, J = 7.6, 2.4 Hz, 1H, H-5'), 7.41 (t, J = 7.6 Hz, 1H, H-4'), 7.12 (s, 1H, H-6'''), 7.01 (d, J = 7.6 Hz, 1H, H-3'''), 6.87 (d, J = 8.0 Hz, 1H, H-4'''), 4.05 (s, 2H, H-2''), 2.29 (s, 3H, CH3-2'''), 2.21 (s, 3H, CH3- 5'''); EIMS (m/z): 375 [M+2]+, 373 [M]+, 253 [C10H6ClN2O2S]+, 225 [C9H6ClN2OS]+, 212 [C8H5ClN2OS]+, 193 [C10H11NOS]+, 179 [C8H4ClN2O]+, 153 [C7H4ClNO]+, 148 [C9H10NO]+, 139 [C7H4ClO]+, 137 [C7H4ClN]+, 121 [C8H11N]+, 111 [C6H4Cl]+, 105 [C8H9]+.
For.: C18H16ClN3O2S; Mol. Wt.:373.8; IR (KBr, cm-1) vmax: 3336 (N-H stretching),3087 (C-H of aromatic ring), 1671 (C=N ofOxadiazole ring), 1653 (C=O), 1563 (C=C aromatic), 1283 (C-O-C bond), 687 (C-Cl bond), 635 (C-S bond ); 1H-NMR (400 MHz, CDCl3, d / ppm): 8.69 (s, 1H, -NH), 7.91 (d, J = 8.4 Hz, 2H, H-3' and H-5'),7.68 (d, J = 7.6 Hz, 1H, H-6'''), 7.46 (d, J = 8.4 Hz,2H, H-2' and 6'), 6.97 (d, J = 7.6 Hz, 1H, H-5'''), 6.96 (s, 1H, H-3'''), 4.04 (s, 2H, CH2-2''), 2.25 (s, 3H, CH3-2'''), 2.20 (s, 3H, CH3-4'''); EIMS (m/z): 375 (4%) [M+2]+, 373 (12%) [M+], 253 (17%), 139 (100%),120 (71%), 111 (37%), 77 (21%).
For.: C18H16ClN3O2S; Mol. Wt.: 373.8; IR (KBr, cm-1) vmax: 3313 (N-H stretching), 3063 (C- H of aromatic ring), 1677 (C=N of Oxadiazole ring),1641 (C=O), 1551 (C=C aromatic), 1263 (C-O-Cbond), 679 (C-Cl bond), 643 (C-S bond); 1H-NMR
1-(Phenylsulfonyl)piperidin-4-carbohydrazide (2): White Crystals; Yield 80%; m.p: 119; Molecular formula: C 12 H 19 N 3 O 3 S; Mol. Wt. 283; IR (KBr, cm -1 ) v max : 3310, 3018, 2926, 1529, 1325, 1630; 1 H-NMR (300 MHz, CDCl 3 Delta / ppm): 7.85 (s, NH-CO), 7.78 (dd, J = 7.8, 1.8 Hz, 2H, H-2', 6'), 7.66-7.63 (m, 3H, H-3' to 5'), 3.79 (t, J = 3.6 Hz, 2H, H eq -2 and 6), 3.75 (t, J = 3.6 Hz, 2H, H ax -2 and 6), 2.12- 1.99 (m, 1H, H-4), 1.79-1.75 (m, 4H, H-3, 5); EIMS m/z (%): 283 (M + , 13), 252 (10), 224 (12), 156 (100), 141 (12), 77 (30); Anal.
5-[1-(Phenylsulfonyl)piperidin-4-yl]-1,3,4- Oxadiazol-2-thiol (3): White powder solid; Yield 88%; m.p: 210- 213; Molecular formula: C 13 H 15 N 3 O 3 S 2 ; Mol. Wt. 325; IR (KBr, cm -1 ) v max : 3035, 2250, 1593, 1326; 1 H-NMR (300 MHz, CDCl 3 Delta / ppm): 7.80 (dd, J = 7.8, 1.8 Hz, 2H, H-2", 6"), 7.67-7.65 (m, 3H, H-3" to 5"), 3.75 (t, J = 3.6 Hz, 2H, H eq -2' and 6'), 3.71 (t, J = 3.6 Hz, 2H, H ax -2' and 6'), 2.80-2.75 (m, 1H, H-4'), 1.80-1.76 (m, 4H, H-3', 5'); EIMS m/z (%): 325 (M + , 8), 252 (14), 224 (10), 157 (14), 156 (100), 141 (14), 82 (93), 77 (31), 55 (12); Anal.