KAPOOR et al., Orient. J. Chem., Vol. 34(5), 2253-2267 (2018)
2257
m, CH ), 2.51 (2H, t, CH ), 4.73 (2H, s, -CH2-NH),
140.59, 155.68, 175.83. ESI-MS: m/z 505 (M+H).
Anal. Calcd. for C H N O S: C, 64.25; H, 8.79; N,
11.10%. Found: C, 64.32; H, 8.62; N, 11.41%.
2
2
5
.6 (1H, s, -CH2-NH), 7.26 [1H, m, CH-(Ar)], 7.47
27
44
4
3
13
[2H, m, 2xCH-(Ar)]. C NMR: (DMSO-d , δ, ppm):
6
1
3
1
4.10, 22.67, 25.69, 27.20, 29.30, 29.64, 31.91,
2.4, 56.95, 77.43, 113.09, 126.09, 140.43, 150.01,
63.03, 177.14.ESI-MS:m/z 515 (M+H).Anal.Calcd.
5-heptadecyl-3-((2-methylpiperazin-1-yl)methyl)-
1,3,4-oxadiazole-2(3H)-thione (M12)
-1
for C H Cl N OS: C, 60.68; H, 8.03; N, 8.17%.
Yield:71%, m.p.:297–299°C, IR:(KBr, cm )
2
6
41
2
3
Found: C, 60.44; H, 8.35; N, 8.48%.
2919 (N-H), 1629 (C=N), 1225 (N-N=C), 1173 (C=S),
1
1
040 (C-O-C). H NMR: (CDCl , δ, ppm): 0.86 (3H,
3
3
-((2,4-dichlorophenylamino)methyl)-5-
t, CH ), 1.17 (3H, d, CH of piperazine), 1.29-1.47
3
3
heptadecyl-1,3,4-oxadiazole-2(3H)-thione (M9)
(32H, m, 16xCH ), 2.14 (1H, s, NH of piperazine),
2
-1
Yield:67%, m.p.:285–287°C, IR:(KBr, cm )
2.55-2.78 [6H, m, 3xCH of piperazine], 3.08 (1H, m,
2
13
2
928 (C-H), 1617 (C=N), 1306 (N-N=C), 1237 (C=S),
CH of piperazine), 3.76 (2H, s, N-CH2-N). C NMR:
1
1102 (C-O-C). H NMR: (CDCl , δ, ppm): 0.86 (3H, t,
(DMSO-d , δ, ppm):14.53, 16.65, 22.63, 25.91, 26.90,
3
6
CH ), 1.10-1.37 (28H, m, 14xCH ), 1.52 (2H, m, CH ),
29.80, 29.49, 30.88, 32.49, 45.67, 47.08, 50.91,
58.73, 65.60, 155.81, 175.93.ESI-MS:m/z453 (M+H).
Anal. Calcd. for C H N OS: C, 66.32; H, 10.69; N,
3
2
2
2
.58 (2H, t, CH ), 4.51 (2H, s, -CH2-NH), 6.09 (1H,
2
s, -CH2-NH), 6.88 [1H, m, 2xCH-(Ar)], 7.35 [1H, m,
25
48
4
13
CH-(Ar)], 7.76 [1H, m, CH-(Ar)]. C NMR: (DMSO-
12.38%. Found: C, 66.15; H, 10.77; N, 12.07%.
d6, δ, ppm):14.66, 22.65, 25.91, 26.30, 29.80, 30.77,
3
1
2.14, 56.97, 117.13, 122.27, 128.68, 129.22, 130.42,
35.90, 155.18, 175.79. ESI-MS: m/z 515 (M+H).
13. 3-((p-toluidino)methyl)-5-heptadecyl-1,3,4-
oxadiazole-2(3H)-thione (M13)
Anal. Calcd. for C H Cl N OS: C, 60.68; H, 8.03; N,
-1
26
41
2
3
Yield:51%, m.p.:274–276°C, IR:(KBr, cm )
8.17%. Found: C, 60.49; H, 8.24; N, 8.05%.
2
920 (N-H), 1660 (C=N), 1335 (N-N=C), 1192 (C=S),
1
1063 (C-O-C). H NMR: (CDCl , δ, ppm): 0.85 (3H,
3
3
-((3,4-dichlorophenylamino)methyl)-5-
t, CH ), 1.12-1.26 (28H, m, 14xCH ), 1.57 (2H, t,
3
2
heptadecyl-1,3,4-oxadiazole-2(3H)-thione (M10)
CH ), 2.18 [3H, s, CH (Ar)], 2.56 (2H, t, CH ), 4.78
2
3
2
Yield: 63%, m.p.: 280–282°C, IR: (KBr,
-
1
(2H, s, CH -NH), 5.45 (1H, s, -CH -NH), 6.86 [2H,
cm ) 2932 (N-H), 1668 (C=N), 1311 (N-N=C), 1152
2
2
1
3
1
m, 2xCH(Ar)], 7.06 [2H, m, 2xCH(Ar)]. C NMR:
DMSO-d , δ, ppm): 14.0, 21.3, 22.6, 25.9, 26.0,
(
C=S), 1054 (C-O-C). H NMR: (CDCl , δ, ppm):
3
(
0.87 (3H, t, CH ), 1.18-1.37 (28H, m, 14xCH ), 1.53
6
3
2
(
2H, m, CH ), 2.66 (2H, t, CH ), 4.89 (2H, s, -CH2-
29.0, 29.4, 32.4, 57.7, 116.9, 129.6, 132.5, 140.99,
155.78, 175.91.ESI-MS:m/z 461 (M+H).Anal.Calcd.
for C H N OS: C, 70.54; H, 9.87; N, 9.14%. Found:
2
2
NH), 5.80 (1H, s, -CH2-NH), 6.67 [1H, m, 2xCH-
(
Ar)], 7.36 [1H, m, CH-(Ar)], 7.88 [1H, m, CH-(Ar)].
27
45
3
1
3
C NMR: (DMSO-d , δ, ppm): 14.51, 22.61, 25.19,
6
C, 70.76; H, 9.68; N, 9.41%.
2
1
1
6.77, 29.10, 29.49, 30.90, 32.44, 57.97, 119.58,
21.15, 125.58, 130.54, 131.68, 140.70, 155.18,
75.93. ESI-MS: m/z 515 (M+H). Anal. Calcd. for
3
1
-((2-bromophenylamino)methyl)-5-heptadecyl-
,3,4-oxadiazole-2(3H)-thione (M14)
C H Cl N OS: C, 60.68; H, 8.03; N, 8.17%. Found:
C, 60.49; H, 8.35; N, 8.29%.
2
6
41
2
3
Yield: 57%, m.p.: 281–283°C, IR: (KBr,
-1
cm ) 2971 (N-H), 1618 (C=N), 1289 (N-N=C), 1201
1
(
C=S), 1061 (C-O-C). H NMR: (CDCl , δ, ppm):
3
5
-heptadecyl-3-((2-methyl-4-nitrophenylamino)
0
.91 (3H, t, CH ), 1.13-1.45 (28H, m, 14xCH ), 1.54
3
2
methyl)-1,3,4-oxadiazole-2(3H)-thione (M11)
(
2H, t, CH ), 2.58 (2H, t, CH ), 4.71 (2H, s, -CH -
2 2 2
Yield: 49%, m.p.: 280–282°C, IR: (KBr,
NH), 5.92 (1H, s, -CH -NH), 6.31 [1H, m, CH-(Ar)],
-
1
2
cm ) 2932 (N-H), 1613 (C=N), 1315 (N-N=C), 1169
6
.91-7.01 [2H, m, 2xCH-(Ar)], 7.34 [1H, m, CH-(Ar)].
1
(C=S), 1020 (C-O-C). H NMR:(CDCl , δ, ppm):0.83
3
13
C NMR: (DMSO-d , δ, ppm): 14.11, 22.66, 25.19,
6
(
3H, t, CH ), 1.22-1.39 (32H, m, 16xCH ), 2.34 (3H,
3
2
26.09, 29.30, 29.47, 30.77, 32.44, 57.17, 113.33,
122.07, 126.73, 128.24, 132.43, 135.42, 155.78,
1
m, Ar-CH ), 4.51 (2H, s, -CH2-NH), 5.74 (1H, s,
3
13
-
(
CH2-NH), 6.52-8.02 [3H, m, 3xCH-(Ar)]. C NMR:
75.98. ESI-MS: m/z 525 (M+H). Anal. Calcd. for
DMSO-d , δ, ppm): 17.17, 22.66, 25.19, 26.80,
C H BrN OS: C, 59.53; H, 8.07; N, 8.01%. Found:
6
26 42
3
29.19, 29.99, 32.42, 57.79, 116.54, 120.12, 127.92,
C, 59.72; H, 8.18; N, 8.33%.