Molecules 2011, 16
8093
(376 MHz, DMSO-d6, δ in ppm): −66.45 (s, 3F, CF3). MS m/z (%): 292; 141; 77 (100). Anal. Calc.
for: C9H7F3N4O2S (292.02) C, 36.99; H, 2.41; N, 19.17; found: C, 37.05; H, 2.25; N, 18.85.
4-Fluoro-N-(5-methyl-1H-1,2,4-triazol-3-yl) benzenesulfonamide (18). Yield: 57%. m.p. 281–283 °C.
IR (KBr, cm−1): 3,107; 1,593; 1,363; 1,188. 1H-NMR (400 MHz, DMSO-d6, δ in ppm): 8.05–7.11 (m,
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4H, H–Ar); 7.24 (s, NH); 1.96 (s, 3H, CH3). C-NMR (100 MHz, DMSO-d6, δ in ppm): 165.66 (d,
J = 253 Hz, C4'); 161.55; 157.24; 132.74; 130.83 (d, J = 10 Hz, C2', C6'); 117.34 (d, J = 24 Hz, C3',
C5'); 13.90. 19F-NMR (376 MHz, DMSO-d6, δ in ppm): −101.57 (s, 1F). MS m/z (%): 256 (100); 95; 75.
Anal. Calc. for: C9H9FN4O2S (256.04) C, 42.18; H, 3.54; N, 21.86; found: C, 30.46; H, 4.54; N, 25.38.
4-Chloro-N-(5-methyl-1H-1,2,4-triazol-3-yl) benzenesulfonamide (19). Yield: 62%. m.p. 219–221 °C.
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IR (KBr, cm−1): 3,468, 3,088; 1,637; 1,384; 1,159; 638. H-NMR (400 MHz, acetone-d6, δ in ppm):
8.04 (d, J = 8 Hz, 2H, H2', H6'); 7.75 (d, J = 8 Hz, 2H, H3', H5'); 6.71 (s, NH); 2.00 (s, 3H, CH3).
13C-NMR (100 MHz, DMSO-d6, δ in ppm): 161.68; 157.31; 140.27; 135.21; 130.13; 129.35; 13.89.
MS m/z (%): 272; 111 (100); 75. Anal. Calc. for: C9H9ClN4O2S (272.01) C, 39.64; H, 3.33; N, 20.54;
found: C, 39.77; H, 3.28; N, 20.56.
4-Bromo-N-(5-methyl-1H-1,2,4-triazol-3-yl) benzenesulfonamide (20). Yield: 62%. m.p. 170–172 °C.
IR (KBr, cm−1): 3,468; 3,022; 1,683; 1,392; 1,188. 1H-NMR (400 MHz, DMSO-d6, δ in ppm): 7.94 (d,
J = 10 Hz, 2H, H3', H5'); 7.89 (d, J = 10 Hz, 2H, H2', H6'); 7.52 (s, NH); 2.00 (s, 3H, CH3).
13C-NMR (100 MHz, DMSO-d6, δ in ppm): 160.18; 156.41; 147.55; 133.17; 130.66; 129.47; 13.56.
MS m/z (%): 318; 252; 219; 157; 75 (100). Anal. Calc. for: C9H9BrN4O2S (351,96) C, 34.08; H, 2.86;
N, 17.67; found: C, 34.05; H, 2.66; N, 17.56.
4-Methyl-N-(5-methyl-1H-1,2,4-triazol-3-yl) benzenesulfonamide (21). Yield: 60%. m.p. 207–209 °C.
IR (KBr, cm−1): 3,468; 3,089; 1,653; 1,363; 1,159. 1H-NMR (400 MHz, DMSO-d6, δ in ppm): 7.85 (d,
J = 8 Hz, 2H, H2', H6'); 7.49 (d, J = 8 Hz, 2H, H3', H5'); 7.23 (s, NH); 2.40 (s, 3H, CH3); 1.97 (s, 3H,
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CH3). C-NMR (100 MHz, DMSO-d6, δ in ppm): 161.20; 157.20; 146.09; 133.62; 130.32; 127.45;
21.14; 13.89. MS m/z (%): 252; 188; 155; 91 (100). Anal. Calc. for: C10H12N4O2S (252.06) C, 47.61;
H, 4.79; N, 22.21; found: C, 48.01; H, 4.56; N, 22.08.
N-(5-Methyl-1H-1,2,4-triazol-3-yl) benzenesulfonamide (22). Yield: 59%. m.p. 167–168 °C. IR (KBr,
1
cm−1): 3,298; 3,005; 1,687; 1,361; 1,188. H-NMR (400 MHz, DMSO-d6, δ in ppm): 7.96–7.67 (m,
5H, H–Ar); 7.26 (s, NH); 1.98 (s, 3H, CH3). 13C-NMR (100 MHz, DMSO-d6, δ in ppm): 161.31;
157.22; 136.49; 135.12; 129.89; 127.36; 13.86. MS m/z (%): 238; 77(100). Anal. Calc. for:
C9H10N4O2S (238,05) C, 45.37; H, 4.23; N, 23.51; found: C, 45.41; H, 4.03; N, 23.36.
4-Fluoro-N-(1H-1,2,4-triazol-3-yl) benzenesulfonamide (23). Yield: 51%. m.p. 174–176 °C. IR (KBr,
cm−1): 3,471; 3,105; 1,649; 1,519; 1,384; 1,139. 1H-NMR (400 MHz, DMSO-d6, δ in ppm): 8.11–7.54
(m, 4H, H–Ar); 7.62 (s, 1H, H5); 7.40 (s, NH). 13C-NMR (100 MHz, DMSO-d6, δ in ppm): 165.69 (d,
J = 254 Hz, C4'); 156.89; 152.71; 132.52; 130.86 (d, J = 10 Hz, C2', C6'); 117.73 (d, J = 23 Hz, C3',
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C5'). F-NMR (376 MHz, DMSO-d6, δ in ppm): −101.73 (s, 1F). MS m/z (%): 242; 159; 95 (100).
Anal. Calc. for: C8H7FN4O2S (242,02) C, 39.67; H, 2.91; N, 23.13; found: C, 39.77; H, 2.68; N, 22.95.