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J = 5.3 Hz, C5CH, pyrazole ring), 7.48 (d, 1H, J = 7.2 Hz, CH5N, pyrazole ring), 6.73–
pyrazole ring), 6.87–7.08 (m, 5H, Ar–H), 7.16–7.29 (m, 4H, Ar–H), 7.38–7.66 (m,
4H, Ar–H); 13C NMR: d 21.4, 109.7, 115.9, 119.8, 123.4, 123.4, 123.9, 124.6, 127.1,
128.0, 128.5, 129.5, 131.4, 132.3, 139.6, 139.8, 145.4, 146.2, 153.9; Elemental
analysis: C22H18N2O3S: calcd. C, 67.67; H, 4.65; N, 7.17; Found: C, 67.77; H, 4.55;
N, 7.10. 5g: Yield: 86%; mp 110–113 8C; IR (KBr, cmÀ1): nmax 3069 (Ar C–H
7.38 (m, 8H, Ar–H), 12.88 (s, 1H, NH); 13C NMR: d 21.4, 98.0, 112.8, 115.9, 116.2,
126.2, 126.3, 126.4, 126.5, 128.2, 128.3, 128.4, 129.0, 133.1, 137.7, 138.5, 142.3,
150.8; Elemental analysis: C16H14N2O3S: calcd. C, 61.13; H, 4.49; N, 8.91; Found:
C, 61.08; H, 4.51; N, 8.74. 5b: Yield: 87%; mp 119–121 8C; IR (KBr, cmÀ1): nmax
3079 (Ar C–H stretch), 2935 (C–H stretch), 1622–1465 (Ar C5C stretch), 1331 (SO3
stretch); 1H NMR: d 2.39 (s, 3H, CH3), 6.23 (d, 1H, J = 7.8 Hz, C5CH, pyrazole ring),
7.55 (d, 1H, J = 7.0 Hz, CH5N, pyrazole ring), 6.73–7.41 (m, 6H, Ar–H), 12.88 (s, 1H,
NH); 13C NMR: d 21.6, 91.5, 93.9, 100.3, 112.6, 116.3, 117.2, 125.2, 126.3, 126.4,
129.0, 133.1, 137.6, 138.5, 142.3, 144.5 152.7; Elemental analysis: C16H12I2N2O3S:
calcd. C, 33.94; H, 2.14; N, 4.95; Found: C, 33.90; H, 2.15; N, 4.92. 5c: Yield: 86%;
mp 167–170 8C; IR (KBr, cmÀ1): nmax 3064 (Ar C–H stretch), 2954 (C–H stretch),
1636–1470 (Ar C5C stretch), 1319 (SO3 stretch); 1H NMR: d 2.35 (s, 3H, CH3), 6.18
(d, 1H, J = 6.4 Hz, C5CH, pyrazole ring), 7.39 (d, 1H, J = 7.5 Hz, CH5N, pyrazole
ring), 7.31–7.47 (m, 6H, Ar–H), 12.61 (s, 1H, NH); 13C NMR: d 21.3, 109.3, 111.7,
118.4, 119.8, 120.2, 123.8, 124.4, 127.3, 129.5, 133.1, 135.3, 138.1, 141.2, 144.8,
152.5; Elemental analysis: C16H12Br2N2O3S: calcd. C, 40.70; H, 2.56; N, 5.93;
Found: C, 40.64; H, 2.46; N, 5.90. 5d: Yield: 85%; mp 112–115 8C; IR (KBr, cmÀ1):
stretch), 2945 (C–H stretch), 1618–1474 (Ar C5C stretch), 1338 (SO3 stretch); 1
H
NMR: d 2.45(s, 3H, CH3), 6.34 (d, 1H, J = 5.5 Hz, C5CH, pyrazole ring), 7.24–7.59
(m, 4H, Ar–H), 7.55 (s, 1H, Ar–H), 7.87 (d, 1H, CH5N, pyrazole ring), 8.16 (s, 1H, Ar–
H); 13C NMR: d 21.6, 91.8, 94.0, 109.8, 118.7, 123.9, 124.1, 127.5, 127.9, 129.6,
133.7, 135.9, 139.9, 140.4, 145.4, 148.0; Elemental analysis: C22H16I2N2O3S: calcd.
C, 41.14; H, 2.51; N, 4.36; Found: C, 41.19; H, 2.57; N, 4.40. 5h: Yield: 90%; mp
135–138 8C; IR (KBr, cmÀ1): nmax 3061 (Ar C–H stretch), 2934 (C–H stretch),
1639–1467 (Ar C5C stretch), 1315 (SO3 stretch); 1H NMR: d 2.45 (s, 3H, CH3), 6.87
(d, 1H, J = 4.8 Hz, C5CH, pyrazole ring), 7.18–7.93 (m, 10H, Ar–H), 7.74 (d, 1H,
J = 5.4 Hz, CH5N, pyrazole ring), 8.04 (s, 1H, Ar–H); 13C NMR: d 21.6, 110.0, 112.9,
118.4, 119.8, 123.8, 127.5, 127.7, 129.6, 133.4, 136.3, 139.3, 144.2, 145.4, 147.2,
155.4; Elemental analysis: C22H16Br2N2O3S: calcd. C, 48.20; H, 2.94; N, 5.11;
Found: C, 48.22; H, 2.84; N, 5.00. 5i: Yield: 85%; mp 117–120 8C; IR (KBr, cmÀ1):
n
max 3078 (Ar C–H stretch), 2965 (C–H stretch), 1643–1466 (Ar C5C stretch), 1330
nmax 3076 (Ar C–H stretch), 2955 (C–H stretch), 1640–1442 (Ar C5C stretch), 1320
(SO3 stretch); 1H NMR: d 2.23 (s, 3H, CH3), 2.39 (s, 3H, CH3), 2.46 (s, 3H, CH3), 6.28
(d, 1H, J = 8.0 Hz, C5CH, pyrazole ring), 7.67 (d, 1H, J = 8.6 Hz, CH5N, pyrazole
ring), 7.39–7.62 (m, 5H, Ar–H), 12.83 (s, 1H, NH); 13C NMR: d 21.3, 25.7, 28.7, 94.9,
101.1, 118.4, 127.1, 127.4, 128.0, 129.7, 135.9, 139.8, 141.6, 146.1, 150.1; Ele-
mental analysis: C18H17IN2O3S: calcd. C, 46.16; H, 3.66; N, 5.98; Found: C, 46.16;
H, 3.65; N, 5.95. 5e: Yield: 90%; mp 114–115 8C; IR (KBr, cmÀ1): nmax 3074 (Ar C–H
(SO3 stretch); 1H NMR: d 2.20 (s, 3H, CH3), 2.41 (s, 3H, CH3), 2.47 (s, 3H, CH3), 6.24
(d, 1H, J = 5.6 Hz, C5CH, pyrazole ring), 6.80 (s, 1H, Ar–H), 7.18–7.29 (m, 5H, Ar–
H), 7.34–7.57 (m, 4H, Ar–H), 7.74 (d, 1H, J = 6.2 Hz, CH5N, pyrazole ring); 13C
NMR: d 21.3, 26.4, 29.5, 94.9, 101.3, 109.5, 114.4, 118.4, 123.7, 126.9, 127.1, 127.7,
128.6, 129.5, 139.7, 140.0, 143.1, 146.2, 150.1; Elemental analysis: C24H21IN2O3S:
calcd. C, 52.85; H, 4.07; N, 5.14; Found: C, 52.87; H, 4.10; N, 5.12. 5j: Yield: 90%;
mp 122–124 8C; IR (KBr, cmÀ1): nmax 3071 (Ar C–H stretch), 2965 (C–H stretch),
1638–1437 (Ar C5C stretch), 1329 (SO3 stretch); 1H NMR: d 2.41 (s, 3H, CH3), 6.33
(d, 1H, J = 7.3 Hz, C5CH, pyrazole ring), 6.69–7.32 (m, 3H, Ar–H), 7.34–7.65 (m, 5H,
Ar–H), 7.68 (d, 1H, J = 8.2 Hz, CH5N, pyrazole ring); 13C NMR: d 21.5, 91.9, 109.7,
117.8, 118.7, 118.7, 127.2, 127.3, 129.6, 130.5, 136.3, 139.9, 140.4, 141.4, 141.5,
145.4, 155.4; Elemental analysis: C22H17ClN2O3S: calcd. C, 62.19; H, 4.03; N, 6.59;
Found: C, 62.27; H, 4.13; N, 6.40.
stretch), 2960 (C–H stretch), 1640–1435 (Ar C5C stretch), 1342 (SO3 stretch); 1
H
NMR: d 2.38 (s, 3H, CH3), 6.29 (d, 1H, J = 6.8 Hz, C5CH, pyrazole ring), 7.45 (d, 1H,
J = 7.0 Hz, CH5N, pyrazole ring), 6.71–7.35 (m, 7H, Ar–H), 12.77 (s, 1H, NH); 13C
NMR: d 21.4, 91.5, 98.4, 115.8, 117.2, 126.3, 126.3, 126.4, 126.5, 128.2, 128.4,
128.5, 129.1, 135.2, 137.3, 138.4, 142.5, 150.9; Elemental analysis:
C
16H13ClN2O3S: calcd. C, 55.09; H, 3.76; N, 8.03; Found: C, 55.10; H, 3.65; N,
8.07. 5f: Yield: 91%; mp 140–142 8C; IR (KBr, cmÀ1): nmax 3066 (Ar C–H stretch),
2975 (C–H stretch), 1648–1477 (Ar C5C stretch), 1333 (SO3 stretch); 1H NMR: d
2.34 (s, 3H, CH3), 6.38 (d, 1H, C5CH, pyrazole ring), 7.81 (d, 1H, J = 7.6 Hz, CH5N,
[24] Indian Pharmacopoeia, Microbiological Assays and Tests, vol. 2, Publication &
Information Directorate, India, 1996, pp. A-100–A-116.