Journal of Sulfur Chemistry
7
4-(phenylamino)benzenesulfonyl azide (Table 2, Entry 4). m.p. 98–100◦C, IR (KBr, cm−1) υ:
3383, 3182, 3056, 3031, 2123(N3), 1666, 1585, 1515, 1496, 1450, 1362(SO2), 1160(SO2), 1088,
829, 746, 700, 592, 557. 1H NMR (400 MHz, DMSO, 25◦C, ppm) δ: 9.23 (br, 1H, NH), 7.79 (d,
2H, J = 8.8 Hz), 7.39 (t, 2H, J = 7.6 Hz), 7.26 (d, 2H, J = 8.0 Hz), 7.17 (d, 2H, J = 8.8 Hz), 7.11
(t, 1H, J = 7.6 Hz). 13C NMR (100 MHz, DMSO,25◦C ppm) δ: 151.2, 140.5, 130.3, 129.9, 124.7,
123.9, 121.2, 114.4 cm−1. EIMS: m/z 274 (M+); 246 [M-N2]+, 230 (90) [M-N2O]+. Elemental
analysis data: C%: 52.65 (calc. 52.54); H%: 3.88 (calc. 3.67); N%: 21.04 (calc. 20.43); S%11.07
(calc. 11.69).
p-Chlorobenzenesulfonyl azide (Table 2, Entry 5). m.p. 36–38◦C, Lit. [26]: 37–38◦C. IR (KBr,
cm−1) υ: 3088, 2345, 2130(N3), 1585, 1478, 1397, 1375(SO2), 1282, 1172(SO2), 1091, 1014,
830, 795, 739, 619, 586. 1H NMR (100 MHz, CDCl3, 25◦C, ppm) δ: 7.9 (d, 2H, J = 8.4 Hz), 7.57
(d, 2H, J = 8.4 Hz).
p-Acethamidobenzenesulfonyl azide (Table 2, Entry 6). m.p. 107–109◦C, Lit. [31]: 108–110◦C.
IR (KBr, cm−1) υ: 3374, 3322, 3277, 3187, 3109, 3056, 2921, 2856, 2128(N3), 1684, 1590, 1532,
1
1404, 1371, 1318(SO2), 1265, 1167(SO2), 1088, 837, 754, 635. H NMR (400 MHz, CDCl3,
25◦C, ppm) δ: 7.93 (d, 2H, J = 8.0 Hz,), 7.82 (d, 2H, J = 8.0 Hz), 7.63 (br, 1H, NH), 2.28 (s, 3H,
CH3).
3-Acethamidobenzenesulfonyl azide (Table 2, Entry 7). m.p. 98–100◦C. IR (KBr, cm−1) υ:
3293, 3252, 3187, 3134, 3089, 2957, 2925, 2852, 2135(N3), 1669, 1597, 1552, 1483, 1372, 1320,
1
1307(SO2), 1163, 1102(SO2), 984, 874, 755, 678. H NMR (400 MHz, CDCl3, 25◦C, ppm) δ:
8.07 (s, 1H, ArH), 8.04 (d, 1H, J = 8.4 Hz), 7.29 (br, 1H, NH), 2.29 (s, 3H, CH3). 13C NMR
(100 MHz, CDCl3, ppm) δ: 191.7, 139.3, 139.0, 130.5, 125.7, 122.7, 117.9, 24.6 cm−1. EIMS:
m/z 240 (M+); 238 [M-2H]+, 197 (95) [M-COCH3]+, 155 (75) [M-COCH3 N3]+. Elemental
analysis data: C%: 40.69 (calc. 40.00); H%: 4.12 (calc. 3.36); N%: 23.08 (calc. 23.32); S%11.07
(calc. 13.29).
1-Naphthalenesulfonyl azide (Table 2, Entry 8). m.p. 51–53◦C, Lit. [32]: 53◦C. IR (KBr, cm−1
)
υ: 3276, 3062, 2345, 2128(N3), 1625, 1592, 1560, 1506, 1366(SO2), 1267, 1173(SO2), 1072,
1
1021, 975, 858, 831, 804, 770, 678, 655. H NMR (400 MHz, CDCl3, 25◦C, ppm) δ: 8.60 (dd,
1H J = 8.8 Hz, J = 0.8 Hz), 8.39 (dd, 1H, J = 7.6 Hz, J = 1.2 Hz), 8.22 (d, 1H, J = 8.0 Hz),
8.02 (d, 1H, J = 8.0 Hz), 7.78 (t, 1H, J = 8.4 Hz), 7.70 (t, 1H, J = 8.0 Hz), 7.63 (t, 1H, J =
8.0 Hz). EIMS: m/z 233 (M+); 231 (75) [M-2H]+, 190 (96) [M-HN3]+, 126 (100) [M-HSO2
N3]+. Elemental analysis data: C%: 52.11 (calc. 51.49); H%: 3.11 (calc. 3.02); N%: 18.54 (calc.
18.02); S%13.23 (calc. 13.75).
2-Naphthalenesulfonyl azide (Table 2, Entry 9). m.p. 44–46◦C, Lit. [33]: 44.2–46◦C. IR
(KBr, cm−1) υ: 3276, 3064, 2124(N3), 1626, 1589, 1515, 1446, 1369, 1352(SO2), 1196, 1170,
1
1130(SO2), 1071, 966, 857, 816, 753, 660, 634, 581, 540. H NMR (400 MHz, CDCl3, 25◦C,
ppm) δ: 8.58 (d, 1H, J = 1.2 Hz), 8.08 (d, 1H, J = 9.2 Hz), 8.06 (d, 1H, J = 9.2 Hz), 8.00 (d, 1H,
J = 8.4 Hz), 7.93 (dd, 1H, J = 8.8 Hz, J = 2 Hz), 7.78–7.74 (ddd, 1H, J = 8.20 Hz, J = 7.00 Hz,
J = 1.20 Hz), 7.73–7.69 (ddd, 1H, J = 8.10 Hz, J = 6.90 Hz, J = 1.20 Hz).
p-Acethamidobenzenesulfonyl azide (Table 2, Entry 10). m.p. 153–155◦C, Lit. [34]: 154–156◦C.
IR (KBr, cm−1) υ: 3284, 3084, 3064, 2132(N3), 1613, 1520, 1437, 1361(SO2), 1296, 1164, 1137,
1114(SO2), 947, 756, 722.