J. Chem. Sci. (2018) 130:23
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6 h. Progress of the reaction was monitored by micro TLC. 2.1i 3-(Dec-9-en-1-yl)-6-nonyl-[1,2,4]triazolo[3,4-b]
After completion of the reaction, reaction mixture was cooled [1,3,4]thiadiazole (6d): The crude compound was sub-
to room temperature and poured onto crushed ice and the title jected to silica gel column chromatography and the required
compound was extracted with ethyl acetate, dried over anhy- product was eluted in a solvent mixture (Hexane: EtOAc,
drous sodium sulphate. The crude compound was subjected to 20: 80, v/v) as an off-white semi solid with 70% yield.
silica gel column chromatography to get the required product. 1H NMR (500 MHz, CDCl3): δ(ppm) = 5.76−5.84(m, 1H,
CH2-CH = CH2), 4.91–5.01(m, 2H, CH2-CH = CH2),
3.02–3.05(t, J = 7.78Hz, 2H, CH2), 2.94–2.97(t, J =
2.1f 3-(Dec-9-en-1-yl)-6-propyl-[1,2,4]triazolo[3,4-b]
7.62Hz, 2H, CH2), 1.99–2.05(m, 2H, CH2), 1.78–1.89(m,
4H, CH2), 1.25–1.43(m, 22H, (CH2)11), 0.91–0.94(t, J =
7.01Hz, 3H, CH3); 13C NMR (100 MHz, CDCl3): δ(ppm) =
169.9, 153.3, 148.1, 139.0, 114.1, 34.0, 33.7, 31.8, 29.6, 29.3,
3 νmax
3418, 2924, 2853, 1719, 1628, 1467, 1377, 1217, 1091, 771;
HR-MS (ESI) m/z [M+H+]: calc for C22H38N4S is 390.2817,
found 391.28885 (C22H39N4S).
[1,3,4]thiadiazole (6a): The crude compound was sub-
jected to silica gel column chromatography and the required
product was eluted in a solvent mixture (Hexane: EtOAc,
20: 80, v/v) as an off-white semi solid with 67% yield.
1H NMR (400 MHz, CDCl3): δ(ppm) = 5.75−5.85(m,
1H, CH2-CH = C H2), 4.91–5.01(m, 2H, CH2-CH =
CH2), 3.02–3.06(t, J = 7.58 Hz, 2H, CH2), 2.92–2.96(t,
J = 7.45 Hz, 2H, CH2), 2.00–2.06(m, 2H, CH2), 1.81–
1.90(m, 2H, CH2), 1.63–1.66(m, 2H, CH2), 1.25–1.41(m,
29.0, 28.8, 28.4, 26.6, 22.6, 14.0; IR (CHCl
cm−1):
10H, (CH2)5), 1.05-1.09(t, J = 7.33Hz, 3H, CH3);13C NMR 2.1j 3,6-Di(dec-9-en-1-yl)-[1,2,4]triazolo[3,4-b][1,3,
(100 MHz, CDCl3): δ(ppm) = 169.3, 153.3, 148.0, 139.0, 4]thiadiazole (6e): The crude compound was subjected to
114.0, 34.1, 33.6, 29.0, 28.9, 28.8, 26.6, 24.9, 21.8, 13.3; IR silica gel column chromatography and the required product
3 νmax
(CHCl
cm−1): 3422, 2925, 2854, 1468, 1216, 758; HR- was eluted in a solvent mixture (Hexane: EtOAc, 20: 80, v/v)
MS (ESI) m/z [M+H+]: calc for C16H26N4S is 306.1878, as an off white semi solid with 65% yield. H NMR (400
1
found 307.19478 (C16H27N4S).
MHz, CDCl3): 5.75–5.85(m, 2H, CH2-CH = CH2), 4.91–
5.01(m, 4H, CH2-CH = CH2), 3.02–3.06(t, J = 7.70 Hz,
4H, CH2), 2.93–2.97(t, J = 7.58 Hz, 4H, CH2), 1.95–
2.04(m, 4H, CH2), 1.76–1.88(m, 4H, CH2), 1.25–1.42(m,
16H, (CH2)8); 13C NMR (125 MHz, CDCl3): δ(ppm) =
169.5, 153.3, 148.0, 139.0, 138.9, 114.1, 114.0, 33.6, 32.4,
32.2, 29.3, 29.0, 28.9, 28.7, 28.4, 26.6, 24.9, 17.8; IR
3 νmax
2.1g 3-(Dec-9-en-1-yl)-6-pentyl-[1,2,4]triazolo[3,4
-b][1,3,4]thiadiazole (6b): The crude compound was
subjected to silica gel column chromatography and the
required product was eluted in a solvent mixture (Hex-
ane: EtOAc, 20: 80, v/v) as an off white semi solid with
63% yield. 1H NMR (500 MHz, CDCl3): δ(ppm) =5.76–
5.84(m, 1H, CH2-CH = CH2), 4.91–5.01(m, 2H, CH2-CH =
CH2), 3.02–3.05(t, J = 7.62Hz, 2H, CH2), 2.95–2.97(t,
J = 7.62Hz, 2H, CH2), 1.99–2.05(m, 2H, CH2), 1.78-
(CHCl
cm−1): 3423, 3016, 2926, 2854, 1473, 1215,
757, 667; HR-MS (ESI) m/z [M+H+]: calc for C23H38N4S
is 402.2817, found 403.28827 (C23H39N4S).
1.89(m, 4H, CH2), 1.25–1.43(m, 14H, (CH2)7), 0.91–0.94(t, 2.1k 3-(Dec-9-en-1-yl)-6-undecyl-[1,2,4]triazolo[3,4
J = 7.01 Hz, 3H, CH3); 13C NMR (100 MHz, CDCl3): -b][1,3,4]thiadiazole (6f): The crude compound was sub-
δ(ppm) = 168.9, 152.9, 147.7, 138.7, 113.7, 33.7, 33.3, 28.7, jected to silica gel column chromatography and the required
3 νmax
28.6, 28.4, 26.3, 24.6, 21.5, 13.0; IR (CHCl
cm−1): product was eluted in a solvent mixture (Hexane: EtOAc, 20:
3417, 2925, 2854, 1630, 1468, 1217, 769; HR-MS (ESI) m/z 80, v/v) as an off white semi solid with 71% yield. 1H NMR
[M+H+]: calc for C18H30N4S is 334.2191, found 335.22604 (500 MHz, CDCl3): δ(ppm) = 5.76−5.84(m, 1H, CH2-
(C18H31N4S).
CH = CH2), 4.91–5.00(m, 2H, CH2-CH = CH2), 3.02–
3.05(t, J = 7.62Hz, 2H, CH2), 2.94–2.97(t, J = 7.62Hz,
2H, CH2), 2.01–2.05(m, 2H, CH2), 1.77–1.89(m, 4H, CH2),
1.26–1.44(m, 26H, (-CH2-)13) 0.86–0.89(t, J = 6.71Hz,
3H, CH3); 13C NMR (100 MHz, CDCl3): δ(ppm) = 169.6,
153.0, 147.8, 138.7, 113.7, 33.7, 33.4, 31.5, 29.3, 29.0, 28.7,
3 νmax
2.1h 3-(Dec-9-en-1-yl)-6-heptyl-[1,2,4]triazolo[3,4
-b][1,3,4]thiadiazole (6c): The crude compound was
subjected to silica gel column chromatography and the
required product was eluted in a solvent mixture (Hexane:
EtOAc, 20: 80, v/v) as an off-white semi solid with 66%
yield. 1H NMR(400MHz, CDCl3):δ(ppm) = 5.75−5.85(m,
1H, CH2-CH = CH2), 4.91–5.01(m, 2H, CH2-CH = CH2),
3.02–3.06(t, J = 7.70Hz, 2H, CH2), 2.93–2.97(t, J =
7.58Hz, 2H, CH2), 1.98–2.06(m, 2H, CH2), 1.77–1.90(m, 4H,
28.4, 28.1, 26.3, 22.3, 13.7; IR (CHCl
cm−1): 3419,
3015, 2925, 2854, 1472, 1215, 759, 667; HR-MS (ESI) m/z
[M+H+]: calc for C24H42N4S is 418.3130, found 419.31976
(C24H43N4S).
CH2), 1.25–1.44(m, 18H, (CH2)9), 0.87–0.91(t, J = 6.84Hz, 2.1l 3-Decyl-6-tridecyl-[1,2,4]triazolo[3,4-b][1,3,4]
3H, CH3); 13C NMR (100 MHz, CDCl3): δ(ppm) = 169.6, thiadiazole(6g): The crude compound was subjected to sil-
153.6, 148.4, 139.3, 114.3, 34.4, 34.0, 29.3, 29.2, 29.1, 26.9, ica gel column chromatography and the required product was
3 νmax
25.2, 22.2, 13.6; IR (CHCl
cm−1): 3418, 2924, 2853, eluted in a solvent mixture (Hexane: EtOAc, 20: 80, v/v) as an
1958, 1711, 1629, 1468, 1217, 771; HR-MS (ESI) m/z off white solid with 69% yield. 1H NMR (500 MHz, CDCl3):
[M+H+]: calc for C20H34N4S is 362.2504, found 363.25755 δ(ppm) = 5.76−5.84(m, 1H, CH2-CH = CH2), 4.91–
(C20H35N4S).
5.01(m, 2H, CH2-CH = CH2), 3.23–3.26 (t, J = 7.62 Hz,