JOURNAL OF SULFUR CHEMISTRY
9
3
3
CH), 6.90 (2 H, d, J = 7.9 Hz, CH), 7.20 (2 H, t, J = 7.7 Hz, 2 CH), 7.92 (1 H, t,
3
3
3
J = 7.8 Hz, 1 CH), 7.95 (1 H, t, J = 7.7 Hz, CH), 8.12 (1 H, d, J = 7.9 Hz, CH), 8.41
3
13
(
(
(
(
1 H, d, J = 7.8 Hz, CH), 9.78 (1 H, s, NH). C NMR (125.7 MHz, Acetone): δ = 120.5
C
2 CH), 121.3 (CH), 126.3 (CH), 128.4 (CH), 129.1 (C), 130.2 (2 CH), 131.6 (CH), 133.7
C), 135.2 (CH), 147.1 (C). MS: m/z (%) = 278 (M+), 201 (11), 156 (20), 137 (39), 77
100), 54 (12). Anal. Calcd for C H N O S (278.28): C, 51.79; H, 3.62; N, 10.07; S, 11.52.
1
2
10
2
4
Found: C, 51.92; H, 3.78; N, 10.19; S, 11.67%.
N-Phenylbenzenesulfonamide (6p)
−
1
Colorless solid, m.p. 109–111°C, 0.21 g, yield: 85%. IR (KBr) (νmax, cm ): 3243, 3057,
1
3
2
991, 1561, 1326, 1140. H NMR (500.1 MHz, Acetone): δ = 6.89 (1 H, t, J = 7.3 Hz,
H
3 3
CH), 6.92 (2 H, d, J = 7.9 Hz, CH), 7.23 (2 H, t, J = 7.7 Hz, 2 CH), 7.49–7.64 (5 H, m,
1
3
5
CH), 8.79 (1 H, s, NH). C NMR (125.7 MHz, Acetone): δ = 118.1 (2 CH), 122.5 (1
C
CH), 126.2 (2 CH), 128.1 (C), 129.4 (2 CH), 130.5 (1 CH), 140.2 (C). MS: m/z (%) = 233
(
M+), 156 (59), 141 (14), 92 (79), 77 (100), 54 (22). Anal. Calcd for C H NO S (233.29):
1
2
11
2
C, 61.78; H, 4.75; N, 6.00; S, 13.74. Found: C, 61.85; H, 4.78; N, 6.13; S, 13.89%.
4
-Methoxy-N-phenylbenzenesulfonamide (6q)
Colorless solid, m.p. 109–112°C, 0.24 g, yield: 90%. IR (KBr) (νmax, cm−1): 3272, 3051,
1
2
(
2
965, 1530, 1324, 1133. H NMR (500.1 MHz, Acetone): δ = 3.86 (3 H, s, OMe), 6.79
H
3
3
3
2 H, d, J = 8.9 Hz, 2 CH), 6.90 (1 H, t, J = 8.1 Hz, 1 CH), 7.05 (2 H, d, J = 7.8 Hz,
3
3
CH), 7.25 (2 H, t, J = 8.0 Hz, 2 CH), 7.53 (2 H, d, J = 8.1 Hz, 2 CH), 8.63 (1 H, s,
13
NH). C NMR (125.7 MHz, Acetone): δ = 57.2 (OMe), 113.2 (2 CH), 121.0 (2 CH),
C
1
23.3 (CH), 128.7 (2 CH), 128.0 (2 CH), 132.0 (2 CH), 135.4 (C), 142.5 (C), 159.4 (C).
MS: m/z (%) = 263 (M+), 186 (69), 171 (11), 107 (81), 77 (100), 54 (20). Anal. Calcd for
C H NO S (263.31): C, 59.30; H, 4.98; N, 5.32; S, 12.18. Found: C, 59.45; H, 4.95; N,
1
3
13
3
5
.35; S, 12.31%.
3-Methyl-N-phenylbenzenesulfonamide (6r)
Colorless solid, m.p. 88–90°C, 0.20 g, yield: 82%. IR (KBr) (νmax, cm−1): 3258, 3062, 2981,
1
1
541, 1324, 1156. H NMR (500.1 MHz, Acetone): δ = 2.37 (3 H, s, Me), 6.94 (2 H, d,
H
3
3
3
J = 7.8 Hz, 2 CH), 7.04 (1 H, t, J = 7.9 Hz, CH), 7.24 (2 H, d, J = 8.0 Hz, 2 CH), 7.48
3
3
(
1 H, d, J = 8.0 Hz, CH), 7.51 (1 H, t, J = 7.8 Hz, CH), 7.69 (1 H, s, CH), 7.79 (1 H, d,
3
13
J = 8.1 Hz, CH), 8.79 (1 H, s, NH). C NMR (125.7 MHz, Acetone): δ = 22.5 (Me),
C
1
1
(
20.6 (2 CH), 123.4 (CH), 124.0 (CH), 127.1 (CH), 129.1 (CH), 129.3 (C), 130.7 (2 CH),
33.1 (CH), 139.5 (C), 140.5 (C). MS: m/z (%) = 247 (M+), 170 (51), 155 (16), 92 (71), 91
51), 77 (100). Anal. Calcd for C H NO S (247.31): C, 63.14; H, 5.30; N, 5.66; S, 12.96.
13 13 2
Found: C, 63.27; H, 5.41; N, 5.72; S, 12.93%.
Acknowledgements
We also gratefully acknowledge from the Iranian Nano Council for the support of this work.