Journal of the Iranian Chemical Society
acetic acid. The reaction mixture was boiled for 10–15 h, the
reaction was monitored by TLC. After removing the solvent,
the residue was washed by water, by solution of alkali and
recrystallized from alcohol.
2-Butylthio-5-[4-(p-nitrobenzylideneamino)
phenyl]-1,3,4-oxadiazole (5d)
Yield 96%, yellow crystals, m.p. 168–169 °C (EtOH),
1
Rf = 0.37; UV, λmax, nm, 290; H NMR (DMSO-d6,
2-Butylthio-5-(4-benzylideneaminophenyl)-1,3,4-oxadia-
zole (5a)
400 MHz, δ, ppm, J/Hz): 0.88 (3H, t, J = 7.4, H-4′), 1.40
(2H, m, H-3′), 1.72 (2H, p, J=7.4, H-2′), 3.26 (2H, t, J=7.2,
H-1′), 7.46 (2H, d, J = 8.6, H-8,10), 7.98 (2H, J = 8.5,
H-7,11), 8.17 (2H, d, J =8.9, H-3″, 5″), 8.33 (2H, J=8.9,
H-2″,6″), 8.81 (1H, s, H-7″). 13C NMR (DMSO-d6 +CDCl3,
100 MHz, δ ppm): 164.75 (C-2), 163.83 (C-5), 121.16 (C-6),
127.52 (C-7, 11), 122.18 (C-8,10), 153.43 (C-9), 31.76
(C-1′), 31.01 (C-2′), 21.08 (C-3′), 13.38 (C-4′), 141.09
(C-1″), 129.93 (C-2″, 6″), 123.97 (C-3″, 5″), 149.07 (C-4″),
160.57 (C-7″). IR, ν, cm−1: 1620 (C=N), 1171 (C–O–C).
Yield 90%, yellow crystals, m.p. 97–98 °C (EtOH),
Rf = 0.30; UV, λmax, nm, 313; 1H NMR (DMSO-d6,
400 MHz, δ, ppm, J/Hz): 0.87 (3H, t, J = 7.4, H-4′), 1.39
(2H, m, H-3′), 1.71 (2H, m, H-2′), 3.19 (2H, t, J=7.3, H-1′),
7.37 (2H, d, J=8.5, H-8,10), 7.50 (3H, m, H-3″,4″,5″), 7.91
(2H, dd, J=8.1, 1.9, H-2″,6″), 7.93 (2H, d, J=8.5, H-7,11),
8.61 (1H, s, H-7″). 13C NMR (DMSO-d6, 100 MHz, δ ppm):
164.92 (C-2), 163.73 (C-5), 120.39 (C-6), 127.57 (C-7, 11),
122.06 (C-8,10), 154.41 (C-9), 31.79 (C-1′), 31.12 (C-2′),
21.06 (C-3′), 13.40 (C-4′), 135.69 (C-1″), 129.01 (C-2″, 6″),
128.94 (C-3″, 5″), 132.02 (C-4″), 162.44 (C-7″). IR, ν, cm−1:
1632 (C=N), 1167 (C–O–C).
2-Benzylthio-5-(4-benzylideneaminophenyl)-1,3,4-oxadia-
zole (6a)
Yield 95%, yellow crystals, m.p. 174–175 °C (EtOH),
1
Rf = 0.38; UV, λmax, nm, 315; H NMR (DMSO-d6,
2-Butylthio-5-[4-(p-chlorobenzylideneamino)
400 MHz, δ, ppm, J/Hz): 4.58 (2H, s, H-7′), 7.25–7.37 (3H,
m, H-3′,4′,5′), 7.43 (2H, d, J = 8.5, H-8,10), 7.48 (2H, d,
J=7.3, H-2′, 6′), 7.50–7.60 (3H, m, H-3″,4″,5″), 7.96 (2H,
dd, J = 7.4, 1.9, H-2″, 6″), 7.99 (2H, d, J = 8.5, H-7, 11),
8.68 (1H, s, H-7″); 13C NMR (DMSO-d6, 100 MHz, δ ppm):
165.13 (C-2), 163.08 (C-5), 120.27 (C-6), 127.62 (C-7,11),
122.07 (C-8,10), 154.50 (C-9), 135.68 (C-1′), 129.01 (C-2′,
6′), 128.62 (C-3′, 5′), 127.81 (C-4′), 136.64 (C-1″), 129.07
(C-2″, 6″), 128.94 (C-3″,5″), 132.03 (C-4″), 162.51 (C-7″).
IR, ν, cm−1: 1626 (C=N), 1170 (C–O–C).
phenyl]-1,3,4-oxadiazole (5b)
Yield 87%, pale yellow crystals, m.p. 135–136 °C (EtOH),
1
Rf = 0.29; UV, um, λmax, nm, 314; H NMR (DMSO-d6,
400 MHz, δ, ppm, J/Hz): 0.87 (3H, t, J = 7.4, H-4′), 1.39
(2H, m, H-3′), 1.70 (2H, p, J=7.4, H-2′), 3.26 (2H, t, J=7.2,
H-1′), 7.38 (2H, d, J = 8.5, H-3″,5″), 7.54 (2H, d, J = 8.5,
H-2″, 6″), 7.92 (2H, d, J=8.4, H-8,10), 7.94 (2H, d, J=8.4,
H-7,11), 8.63 (1H, s, H-7″). 13C NMR (DMSO-d6, 100 MHz,
δ ppm): 164.75 (C-2), 163.55 (C-5), 120.45 (C-6), 127.39
(C-7, 11), 121.85 (C-8,10), 153.91 (C-9), 31.74 (C-1′), 30.91
(C-2′), 20.85 (C-3′), 13.12 (C-4′), 134.42 (C-1″), 130.38
(C-2″, 6″), 128.86 (C-3″, 5″), 136.42 (C-4″), 160.91 (C-7″).
IR, ν, cm−1: 1625 (C=N), 1171 (C–O–C).
2-Benzylthio-5-[4-(p-chlorobenzylideneamino)
phenyl]-1,3,4-oxadiazole (6b)
Yield: 85%, yellow crystals, m.p. 211–212 °C (EtOH),
1
2-Butylthio-5-[4-(p-dimethylaminobenzylideneamino)
phenyl]-1,3,4-oxadiazole (5c)
Rf = 0.25; UV, λmax, nm, 319; H NMR (DMSO-d6,
400 MHz, δ, ppm, J/Hz): 4.54 (2H, s, H-7′), 7.24–7.47 (7H,
m, H-8,10, 2′, 3′, 4′, 5′, 6′), 7.94 (2H, d, J = 7.8, H-7,11),
8.04 (2H, d, J= 8.1, H-2″, 6″), 8.29 (2H, d, J= 8.8, H-3″,
5″), 8.65 (1H, s, H-7″); IR, ν, cm−1: 1627 (C=N), 1170
(C–O–C).
Yield 81%, red–orange crystals, m.p. 158–159 °C (EtOH),
1
Rf = 0.63; UV, λmax, nm, 381; H NMR (DMSO-d6,
400 MHz, δ, ppm, J/Hz): 0.87 (3H, t, J=7.3, H-4′), 1.39 (2H,
m, H-3′), 1.70 (2H, p, J=7.4, H-2′), 2.97 (6H, s, N(CH3)2),
3.25 (2H, t, J = 7.2, H-1′), 6.74 (2H, d, J = 8.9, H-3″,5″),
7.28 (2H, J = 8.5, H-8,10), 7.71 (2H, J = 8.9, H-2″,6″),
7.88 (2H, d, J=8.5, H-7,11), 8.39 (1H, s, H-7″). 13C NMR
(DMSO-d6, 100 MHz, δ ppm): 164.91 (C-2), 163.17 (C-5),
119.10 (C-6), 127.23 (C-7, 11), 121.55 (C-8,10), 152.01
(C-9), 31.72 (C-1′), 30.90 (C-2′), 20.70 (C-3′), 12.96 (C-4′),
123.34 (C-1″), 130.42 (C-2″, 6″), 111.28 (C-3″, 5″), 155.24
(C-4″), 160.93 (C-7″, 39.40 ((CH3)2N). IR, ν, cm−1: 1623
(C=N), 1162 (C–O–C).
2-Benzylthio-5-[4-(p-dimethylaminobenzylideneamino)
phenyl]-1,3,4-oxadiazole (6c)
Yield 84%, pale brown crystals, m.p. 159–160оС (EtOH),
Rf = 0.46; UV, λmax, nm, 382; 1H NMR (DMSO-d6,
400 MHz, δ, ppm, J/Hz): 3.03 (6H, s, N–(CH3)2), 4.59
(2H, s, H-7′), 6.80 (2H, d, J = 8.9, H-8,10), 7.29 (1H, t,
J = 7.3, H-4′), 7.35 (2H, d, J = 7.8, H-3′,5′), 7.36 (2H, d,
1 3