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Med Chem Res (2012) 21:1660–1664
added slowly with constant stirring at room temperature.
The reaction mixture was then refluxed for 3–4 h. The
solution was poured into ice-cold water, and the product
was recrystallized by using ethanol.
(C=S), 1342 cm-1 (–C–N), 1371, 1142 cm-1 (–SO2),
1132 cm-1 (–F).
Compound 6e
Yield 70%, white; mp 224°C; Anal. Calcd for C22H19N9O4S3
(569.63): C, 46.39%; H, 3.36%; N, 22.13%. found: C,
46.17%; H, 3.14%; N, 22.01%; NMR CDCl3: 4.28 (s, 2H,
CH2), 7.11 (s, 1H, Ar–NH), 8.62 (s, 1H, CSNH), 9.08 (s, 1H,
CONH), 7.42–8.21 (m, 8H, Ar–H), 6.11 (s, 2H, Ar–NH2), IR
(KBr)/cm-1: 3318 cm-1 (–NH2–), 3163 cm-1 (–NH–),
1682 cm-1 ([C=O), 1613 cm-1 (–C=N–), 1210 cm-1
(C=S), 1343 cm-1 (–C–N), 1357, 1150 cm-1 (–SO2).
Spectral data of compounds 6(a–j)
Compound 6a
Yield 70%, brown; mp 186°C; Anal. Calcd for
C21H16ClN9O3S3 (574.05): C, 43.94%; H, 2.96%; N, 21.80%.
found: C, 43.77%; H, 2.65%; N, 21.80%; NMR CDCl3: 4.26
(s, 2H, CH2), 7.12 (s, 1H, Ar–NH), 8.59 (s, 1H, CSNH), 9.07
(s, 1H, CONH), 7.40–8.10 (m, 8H, Ar–H), 6.10 (s, 2H,
Ar–NH2), IR (KBr)/cm-1: 3320 cm-1 (–NH2–), 3173 cm-1
(–NH–), 1682 cm-1 ([C=O), 1625 cm-1 (–C=N–),
1210 cm-1 (C=S), 1339 cm-1 (–C–N), 1368,1150 cm-1
(–SO2), 759 cm-1 (–Cl).
Compound 6f
Yield 69%, brown; mp 169°C; Anal. Calcd for
C21H16ClN9O3S3 (574.05): C, 43.94%; H, 2.81%; N, 21.96%.
found: C, 43.77%; H, 2.62%; N, 21.72%; NMR CDCl3: 4.00
(s, 2H, CH2), 7.30 (s, 1H, Ar–NH), 8.45 (s, 1H, CSNH), 9.09
(s, 1H, CONH), 7.80–8.20 (m, 9H, Ar–H), 6.10 (s, 2H,
Ar–NH2), IR (KBr)/cm-1: 3310 cm-1 (–NH2–), 3198 cm-1
(–NH–), 1696 cm-1 ([C=O), 1637 cm-1 (–C=N–),
1203 cm-1 (C=S), 757 cm-1 (–Cl), 1367, 1152 cm-1 (–SO2).
Compound 6b
Yield 68%, yellow; mp 146°C; Anal. Calcd for
C21H16N10O5S3 (584.61): C, 43.14%; H, 2.76%; N, 23.96%.
found: C, 43.01%; H, 2.59%; N, 23.82%; NMR CDCl3: 4.27
(s, 2H, CH2), 7.11 (s, 1H, Ar–NH), 8.60 (s, 1H, CSNH), 9.06
(s, 1H, CONH), 7.36–8.11 (m, 8H, Ar–H), 6.11 (s, 2H,
Ar–NH2), IR (KBr)/cm-1: 3311 cm-1 (–NH2–), 3172 cm-1
(–NH–), 1680 cm-1 ([C=O), 1617 cm-1 (–C=N–), 1205 cm-1
(C=S), 1340 cm-1 (–C–N), 1367, 1152 cm-1 (–SO2), 1570,
1281 cm-1 (–NO2).
Compound 6g
Yield 67%, green; mp 180°C; Anal. Calcd for C22H19N9O3S3
(553.63): C, 47.73%; H, 3.46%; N, 22.77%. found: C,
47.54%; H, 3.29%; N, 22.63%; NMR CDCl3: 4.12 (s, 2H,
CH2), 7.11 (s, 1H, Ar–NH), 8.62 (s, 1H, CSNH), 9.04 (s, 1H,
CONH), 7.50–8.11 (m, 8H, Ar–H), 6.14 (s, 2H, Ar–NH2), IR
(KBr)/cm-1: 3315 cm-1 (–NH2–), 3182 cm-1 (–NH–),
1689 cm-1 ([C=O), 1622 cm-1 (–C=N–), 1216 cm-1 (C=S),
1339 cm-1 (–C–N), 1368, 1152 cm-1 (–SO2).
Compound 6c
Yield 72%, light yellow; mp 169°C; Anal. Calcd for
C21H16N10O5S3 (584.61): C, 43.14%; H, 2.76%; N, 23.96%.
found: C, 43.01%; H, 2.61%; N, 23.72%; NMR CDCl3: 4.25
(s, 2H, CH2), 7.10 (s, 1H, Ar–NH), 8.62 (s, 1H, CSNH), 9.08
(s, 1H, CONH), 7.38–8.15 (m, 8H, Ar–H), 6.15 (s, 2H, Ar–
NH2), IR (KBr)/cm-1: 3314 cm-1 (–NH2–), 3165 cm-1
(–NH–), 1684 cm-1 ([C=O), 1615 cm-1 (–C=N–),
1211 cm-1 (C=S), 1337 cm-1 (–C–N), 1365, 1148 cm-1
(–SO2), 1568, 1277 cm-1 (–NO2).
Compound 6h
Yield 70%, light yellow; mp 152°C; Anal. Calcd for
C21H16N10O5S3 (584.61): C, 43.14%; H, 2.76%; N, 23.96%.
found: C, 43.01%; H, 2.61%; N, 23.76%; NMR CDCl3: 4.17
(s, 2H, CH2), 7.12 (s, 1H, Ar–NH), 8.52 (s, 1H, CSNH), 9.13
(s, 1H, CONH), 7.32–8.15 (m, 8H, Ar–H), 6.12 (s, 2H,
Ar–NH2), IR (KBr)/cm-1: 3316 cm-1 (–NH2–), 3183 cm-1
(–NH–), 1687 cm-1 ([C=O), 1615 cm-1 (–C=N–),
1211 cm-1 (C=S), 1330 cm-1 (–C–N), 1362, 1153 cm-1
(–SO2), 1558, 1287 cm-1 (–NO2).
Compound 6d
Yield 73%, gray; mp 182°C; Anal. Calcd for C21H16FN9O3S3
(557.60): C, 45.23%; H, 2.89%; N, 22.61%. found: C,
45.05%; H, 2.67%; N, 22.47%; NMR CDCl3: 4.25 (s, 2H,
CH2), 7.21 (s, 1H, Ar–NH), 8.59 (s, 1H, CSNH), 9.05 (s, 1H,
CONH), 7.32–8.16 (m, 8H, Ar–H), 6.13 (s, 2H, Ar–NH2),
IR (KBr)/cm-1: 3321 cm-1 (–NH2–), 3168 cm-1 (–NH–),
1685 cm-1 ([C=O), 1612 cm-1 (–C=N–), 1215 cm-1
Compound 6i
Yield 68%, brown; mp196°C; Anal. Calcd for C22H19N9O4S2
(569.63): C, 46.39%; H, 3.36%; N, 22.13%. found: C,
46.18%; H, 3.18%; N, 22.01%; NMR CDCl3: 4.18 (s, 2H,
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