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(s, 1H); 13C NMR: 21.7 (CH3), 38.3 (CH2), 120.4, 122.6,
123.1, 128.6, 130.8, 140.1, 149.8 (S–C=N), 164.6 (C, tri-
azine), 167.2 (C, triazine), 174.1 (C, triazine); MS (EI) m/z:
363 (M?). Anal. Calcd. for C18H17N7S: C, 59.49; H, 4.71;
N, 26.98; found: C, 59.33; H, 4.84; N, 26.66.
6-[(1H-benzo[d]imidazol-2-ylthio)methyl]-N2-p-tolyl-
1,3,5-triazine-2,4-diamine (5b)
Recrystallization from ethanol gave white solid (214 mg,
59%) of m.p. 95–98°C; IR (neat): 3568, 3380, 3345, 1625;
1H NMR: 2.32 (s, 3H), 4.43 (s, 2H), 7.04 (brs, 2H),
7.13–7.20(m, 4H), 7.47 (brs, 2H), 7.60 (brs, 2H), 9.50
(s, 1H); MS (EI) m/z: 363 (M?). Anal. Calcd. for
C18H17N7S: C, 59.49; H, 4.71; N, 26.98; found: C, 59.62;
H, 4.59; N, 28.84.
6-[(5-Methyl-1H-benzo[d]imidazol-2-yl thio)methyl]-N2-
p-tolyl-1,3,5-triazine-2,4-diamine (5g)
Recrystallization from methanol gave white solid (219 mg,
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58%) of m.p. 120–121°C, IR (KBr): 3614, 3390, 3396; H
6-[(1H-benzo[d]imidazol-2-ylthio)methyl]-N2-
(4-chlorophenyl)-1,3,5-triazine-2,4-diamine (5c)
NMR: 2.23 (s, 3H), 2.39 (s, 3H), 4.32 (s, 2H), 6.96 (d, 1H,
J = 8.4 Hz), 6.66–6.77 (m, 2H), 7.22 (brs, 3H), 7.39
(s, 1H), 7.65 (s, 2H), 9.46 (s, 1H), 12.47 (s, 1H); MS (EI)
m/z: 377 (M?). Anal. Calcd. for C19H19N7S: C, 60.46; H,
5.07; N, 25.98; found: C, 60.73; H, 4.98; N, 26.11.
Recrystallization from DMF gave white solid (218 mg,
57%) of m.p. 118–120°C, 1H NMR: 4.39 (s, 2H),
7.13–7.14 (m, 3H), 7.26–7.29 (m, 3H), 7.46 (brs, 2H), 7.74
(brs, 2H), 9.71 (s, 1H), 12.76 (s, 1H); MS (EI) m/z: 383
(M?). Anal. Calcd. for C17H14ClN7S: C, 53.19; H, 3.68; N,
25.54; found: C, 53.22; H, 3.59; N, 25.64.
N2-(4-chlorophenyl)-6-((5-methyl-1H-benzo[d]imidazol-2-
ylthio)methyl)-1,3,5-triazine-2,4-diamine (5h)
Recrystallization from ethanol gave pale brown solid
(194 mg, 49%) of m.p. 107–110°C; 1H NMR: 2.34 (s, 3H),
4.35 (s, 2H), 6.96 (s, 1H), 7.18 (brs, 3H), 7.31 (d, 2H,
J = 8 Hz), 7.40 (d, 1H, J = 8), 7.72 (brs, 2H), 9.70
(s, 1H), 12.44 (s, 1H); MS (EI) m/z: 397 (M?). Anal. Calcd.
for C18H16ClN7S: C, 54.34; H, 4.05; N, 24.64; found: C,
54.72; H, 3.87; N, 24.93.
6-[(1H-benzo[d]imidazol-2-ylthio)methyl]-N2-
(4-methoxyphenyl)-1,3,5-triazine-2,4-diamine (5d)
Recrystallization from methanol gave white solid (203 mg,
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54%) of m.p. 141–143°C, H NMR: 3.70 (s, 3H), 4.35
(s, 2H), 6.80 (brs, 2H), 7.12–7.14 (m, 4H), 7.47 (s, 3H),
7.59 (s, 1H), 9.43 (s, 1H), 12.68 (s, 1H); MS (EI) m/z: 379
(M?). Anal. Calcd. for C18H17N7OS: C, 56.98; H, 4.52; N,
25.84; found: C, 56.69; H, 4.43; N, 25.56.
N2-(4-methoxyphenyl)-6-((5-methyl-1H-benzo[d]imidazol-
2-ylthio)methyl)-1,3,5-triazine-2,4-diamine (5i)
Recrystallization from methanol gave white solid (283 mg,
6-[(1H-benzo[d]imidazol-2-ylthio)methyl]-N2-o-tolyl-
1,3,5-triazine-2,4-diamine (5e)
72%) of m.p. 131–133°C, IR (KBr): 3614, 3390, 3396,
1640; H NMR: 2.40 (s, 3H), 3.71 (s, 3H), 4.33 (s, 2H),
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6.76 (brs, 3H), 6.79 (d, 1H, J = 8 Hz), 6.96 (d, 1H,
J = 8 Hz), 7.19–7.37 (m, 2H), 7.52 (d, 2H, J = 8 Hz),
9.39 (s, 1H), 12.47 (s, 1H); MS (EI) m/z: 393 (M?). Anal.
Calcd. for C19H19N7OS: C, 58.00; H, 4.87; N, 24.92;
found: C, 57.81; H, 4.67; N, 25.13.
Recrystallization from methanol/DMF gave white solid
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(221 mg, 61%) of m.p. 95–97°C, H NMR: 2.19 (s, 3H),
4.32 (s, 2H), 7.01 (brs, 3H), 7.07 (d, 1H, J = 6.8 Hz),
7.13–7.12 (m, 2H), 7.20 (d, 1H, J = 6.8 Hz), 7.32 (d, 1H,
J = 6.8 Hz), 7.40 (brs, 1H), 7.51 (brs, 1H), 8.91 (s, 1H),
12.68 (s, 1H); MS (EI) m/z: 363 (M?). Anal. Calcd. for
C18H17N7S: C, 59.49; H, 4.71; N, 26.98; found: C, 59.67;
H, 4.61; N, 26.77.
6-[(5-Methyl-1H-benzo[d]imidazol-2-ylthio)methyl]-N2-
o-tolyl-1,3,5-triazine-2,4-diamine (5j)
Recrystallization from methanol/DMF gave white solid
(230 mg, 61%) of m.p. 111–113°C, IR (KBr): 3620, 3390,
3370, 1625; 1H NMR: 2.19 (s, 3H), 2.39 (s, 3H), 4.29
(s, 2H), 6.98 (d, 2H, J = 8 Hz), 7.06–7.08 (m, 2H), 7.12
(d, 1H, J = 8 Hz), 7.19–7.26 (m, 2H), 7.33 (d, 1H,
J = 8 Hz), 7.39 (d, 1H, J = 8 Hz), 8.91 (s, 1H), 12.49
(s, 1H); MS (EI) m/z: 377 (M?). Anal. Calcd. for C19H19N7S:
C,60.46;H,5.07;N,25.98;found:C,60.24;H, 5.27;N,25.76.
6-[(5-Methyl-1H-benzo[d]imidazol-2-yl thio)methyl]-N2-
phenyl-1,3,5-triazine-2,4-diamine (5f)
Recrystallization from methanol/DMF gave white solid
(250 mg, 69%) of m.p. 156–158°C, IR (KBr): 3614, 3390,
3323; H NMR: 2.68 (s, 3H), 4.35 (s, 2H), 6.95 (d, 1H,
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J = 6.8 Hz), 7.01–7.03 (m, 2H), 7.21–7.24 (m, 4H), 7.34
(d, 1H, J = 6.8 Hz), 7.73 (brs, 2H), 9.58 (s, 1H), 12.68
123