Synthesis and antibacterial activity of novel 4-chloro-2-mercaptobenzenesulfonamide derivative 43
(0.24 g) at reflux for 8 h, the title compound 16 was
(21): Starting from 10 (1.06 g) and benzyl hydrazinecar-
bodithioate (0.40 g) at reflux for 8.5 h, the title compound
21 was obtained. Yield: 0.63 g, 46%, mp 253°C–256°C
dec.; IR νmax (KBr)/cm−1 3342, 3217 (NH), 2923, 2759
(CH3, CH2), 1660 (C=O), 1599, 1578, 1544 (C=N), 1313,
1143 (SO2); 1H NMR δ (DMSO-d6) 4.40 (s, 2H, SCH2), 4.42
(s, 2H, SCH2), 7.20–7.36 (m, 12H, 2 x Ph and 4-ClC6H4),
7.71 (d, J= 7.3 Hz, 2H, 4-ClC6H4), 7.73 (s, 1H, H-3), 7.98
(s, 1H, H-6), 10.75 (s, 1H, NHCO), 14.40 (s, 1H, SO2NH).
Anal. Calcd. for C29H22Cl2N4O3S4: C, 51.70; H, 3.29; N, 8.32.
Found: C, 51.55; H, 3.19; N, 8.24%.
4-Benzylthio-2-chloro-5-(5-methylthio-1,3,4-thiadi-
azol-2-yl-aminosulfonyl)-N-(4-methylphenyl)benzamide
(22): Starting from 11 (1.02 g) and methyl hydrazinecar-
bodithioate (0.24 g) at reflux for 9 h, the title compound
22 was obtained. Yield: 0.45 g, 37%, mp 237°C–240°C
dec.; IR νmax (KBr)/cm−1 3411, 3278 (NH); 2922 (CH3, CH2),
1652 (C=O), 1580, 1543 (C=N), 1318, 1141 (SO2); 1H NMR
δ (DMSO-d6) 2.27 (s, 3H, CH3), 2.62 (s, 3H, SCH3), 4.44 (s,
2H, SCH2), 7.16 (d, J= 8.4 Hz, 2H, 4-MeC6H4), 7.23–7.33
(m, 5H, Ph), 7.56 (d, J= 8.4 Hz, 2H, 4-MeC6H4), 7.72 (s, 1H,
H-3), 7.97 (s, 1H, H-6), 10.52 (s, 1H, NHCO), 14.40 (br s,
1H, SO2NH). Anal. Calcd. for C24H21ClN4O3S4: C, 49.94; H,
3.67; N, 9.71. Found: C, 49.75; H, 3.45; N, 9.96%.
4-Benzylthio-5-(5-benzylthio-1,3,4-thiadiazol-2-yl-
aminosulfonyl)-2-chloro-N-(4-methylphenyl)benzamide
(23): Starting from 11 (1.02 g) and benzyl hydrazinecar-
bodithioate (0.40 g) at reflux for 8 h, the title compound
23 was obtained. Yield: 0.63 g, 48%, mp 222°C–224°C
dec.; IR νmax (KBr)/cm−1 3286, 3137 (NH), 2921, 2847 (CH3,
CH2), 1656 (C=O), 1583, 1545, 1518 (C=N), 1322, 1151
(SO2); 1H NMR δ (DMSO-d6) 2.27 (s, 3H, CH3), 4.41 (s, 4H,
2 x SCH2), 7.16 (d, J= 8.3 Hz, 2H, 4-MeC6H4), 7.22–7.36
(m, 10H, 2 × Ph), 7.57 (d, J= 8.3 Hz, 2H, 4-MeC6H4), 7.72
(s, 1H, H-3), 7.95 (s, 1H, H-6), 10.52 (s, 1H, NH), 14,40 (br
s, 1H, SO2NH). Anal. Calcd. for C30H25ClN4O3S4: C, 55.16;
H, 3.86; N, 8.58. Found: C, 55.10; H, 3.82; N, 8.58%.
Methyl-4-benzylthio-2-chloro-5-(5-methylthio-1,3,4-
thiadiazol-2-yl-aminosulfonyl)benzoate(24):Startingfrom
12 (0.87g) and methyl hydrazinecarbodithioate (0.24g) at
reflux for 9h, the title compound 24 was obtained. Yield:
0.43g, 43%, mp 171°C–173°C dec.; IR νmax (KBr)/cm−1 3360
(NH), 2850 (CH3, CH2), 1731 (C=O), 1577, 1542 (C=N),
1314, 1150 (SO2); 1H NMR δ (DMSO-d6) 2.61 (s, 3H, SCH3),
3.86 (s, 3H, OCH3), 4.41 (s, 2H, SCH2), 7.32 (s, 5H, Ph,), 8.32
(s, 1H, H-3), 8.34 (s, 1H, H-6), 14.40 (br s, 1H, NH). Anal.
Calcd. for C18H16ClN3O4S4: C, 43.06; H, 3.21; N, 8.37. Found:
C, 42.99; H, 3.19; N, 8.38%.
obtained. Yield: 0.55 g, 60%, mp 178°C–180°C dec.; IR
νmax (KBr)/cm−1 3127 (NH), 2921, 2855 (CH3, CH2), 1543
1
(C=N), 1305, 1150 (SO2); H NMR δ (DMSO-d6) 2.33 (s,
3H, CH3), 2.62 (s, 3H, SCH3), 4.31 (s, 2H, SCH2), 7.22-7.27
(m, 5H, Ph), 7.58 (s, 1H, H-3), 7.88 (s, 1H, H-6), 14.30 (br
s, 1H, SO2NH). Anal. Calcd. for C17H16ClN3O2S4: C, 44.58;
H, 3.52; N, 9.17. Found: C, 44.21; H, 3.38; N, 8.90%.
2-Benzylthio-4-chloro-5-methyl-N-(5-benzylthio-1,3,4-
thiadiazol-2-yl)benzenesulfonamide (17): Starting from
7 (0.78 g) and benzyl hydrazinecarbodithioate (0.40 g) at
reflux for 8 h, the title compound 17 was obtained. Yield:
0.45 g, 42%, mp 194°C–196°C dec.; IR νmax (KBr)/cm−1
3441 (NH), 2921, 2852 (CH3, CH2), 1554 (C=N)), 1310,
1297, 1137 (SO2); 1H NMR δ (DMSO-d6) 2.31 (s, 3H, CH3),
4.26 (s, 2H, SCH2), 4.31 (s, 2H, SCH2), 7.27–7.35 (m, 10H,
arom.), 7.42 (s, 1H, H-3), 7.79 (s, 1H, H-6). Anal. Calcd. for
C23H20ClN3O2S4: C, 51.72; H, 3.77; N, 7,87. Found: C, 51.40;
H, 3.68; N, 7.55%.
4-Benzylthio-2-chloro-5-(5-methylthio-1,3,4-thiadiaz-
ol-2-yl-aminosulfonyl)-N-phenylbenzamide (18): Starting
from 9 (0.99 g) and methyl hydrazinecarbodithioate
(0.24 g) at reflux for 8.5 h, the title compound 18 was
obtained. Yield: 0.50 g, 44%, mp 266°C–269°C dec.; IR
ν
max (KBr)/cm−1 3275 (NH), 2879 (CH3, CH2), 1659 (C=O),
1
1583, 1544 (C=N), 1322, 1139 (SO2); H NMR δ (DMSO-
d6) 2.63 (s, 3H, SCH3), 4.45 (s, 2H, SCH2), 7.11–7.38 (m,
8H, arom.), 7.67–7.69 (d, 2H, arom.), 7.73 (s, 1H, H-3),
7.99 (s, 1H, H-6), 10.61 (s, 1H, NHCO), 14,40 (br s, 1H,
SO2NH). Anal. Calcd. for C23H19ClN4O3S4: 49.06; H, 3.40;
N, 9.95. Found: 49.02; H, 3.44; N, 9.97%.
4-Benzylthio-2-chloro-5-(5-benzylthio-1,3,4-thiadiaz-
ol-2-yl-aminosulfonyl)-N-phenylbenzamide (19): Starting
from 9 (0.99 g) and benzyl hydrazinecarbodithioate
(0.40 g) at reflux for 9 h, the title compound 19 was
obtained. Yield: 0.66 g, 51%, mp 231°C–233°C dec.; IR
νmax (KBr)/cm−1 3314, 3137 (NH), 2854 (CH3, CH2), 1663
(C=O), 1582 (C=N), 1324, 1151 (SO2); 1H NMR δ (DMSO-
d6) 4.41 (s, 4H, 2 × SCH2), 7.08-7.39 (m, 13H, arom.),
7.66–7.71 (m, 3H, H-3 and arom.), 7.96 (s, 1H, H-6), 10.61
(s, 1H, NHCO), 14.45 (br s, 1H, SO2NH). Anal. Calcd. for
C29H23ClN4O3S4: 54.49; H, 3.63; N, 8.76. Found: 54.60; H,
3.73; N, 8.87%.
4-Benzylthio-2-chloro-5-(5-methylthio-1,3,4-thiadi-
azol-2-yl-aminosulfonyl)-N-(4-chlorophenyl)benzamide
(20): Starting from 10 (1.06 g) and methyl hydrazinecar-
bodithioate (0.24 g) at reflux for 8 h, the title compound
20 was obtained. Yield: 0.55 g, 45%, mp 256°C–258°C
dec.; IR νmax (KBr)/cm−1 3279 (NH), 2923, 2841 (CH3,
CH2), 1659 (C=O), 1581, 1545 (C=N), 1311, 1140 (SO2); 1H
NMR δ (DMSO-d6) 2.63 (s, 3H, SCH3), 4.45 (s, 2H, SCH2),
7.27–7.36 (m, 5H, Ph), 7.42 (d, J= 7.8 Hz, 2H, 4-ClC6H4),
7.71 (d, J= 7.8 Hz, 2H, 4-ClC6H4), 7.74 (s, 1H, H-3), 8.01 (s,
1H, H-6), 10.75 (s, 1H, NHCO), 14.40 (br s, 1H, SO2NH).
Anal. Calcd. for C23H18Cl2N4O3S4: C, 46.23; H, 3.04; N, 9.38.
Found: C, 46.01; H, 2.89; N, 8.71%.
2-Benzylthio-4-chloro-5-methyl-N-(5-pyrrolidin-1-yl-
1,3,4-thiadiazol-2-yl)benzenesulfonamide (25): Starting
from 7 (0.78 g) and pyrrolidine-1-carbothiohydrazide
(0.29 g) at reflux for 29 h, the title compound 25 was
obtained. Yield: 0.56 g, 59%, mp 220°C–223°C dec.; IR νmax
(KBr)/cm−1 3247 (NH), 2926, 2859 (CH3, CH2), 1527(C=N),
1342, 1139 (SO2); 1H NMR δ (DMSO-d6) 1.93–1.96 (m, 4H,
CH2), 2.33 (s, 3H, CH3), 3.30–3.34 (m, 4H, CH2), 4.31 (s, 2H,
SCH2), 7.26–7.34 (m, 5H, Ph), 7.54 (s, 1H, H-3), 7.86 (s, 1H,
H-6), 13.23 (s, 1H, NH). Anal. Calcd. for C20H21ClN4O2S3:
4-Benzylthio-5-(5-benzylthio-1,3,4-thiadiazol-2-yl-
aminosulfonyl)-2-chloro-N-(4-chlorophenyl)benzamide
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