Molecules 2001, 6
491
layer chromatography. Compound 4: 1H-NMR (400 MHz, CD3OD): δ 2.43 (s, 3H), 4.65 (dt, J=5.3, 0.6
Hz, 2H), 5.06 (dd, J=17.3, 0.6 Hz, 1H), 5.20 (dd, J=10.3, 0.6 Hz, 1H), 5.90 (ddt, J=15.6, 10.3, 5.2 Hz,
13
1H), 7.32-7.41 (m, 3H), 8.04-8.06 (m, 2H) ppm; C-NMR (100 MHz, CD3OD): δ 11.9, 50.9, 116.8,
126.1, 129.0, 131.0, 131.9, 132.3, 152.9, 160.7 ppm; GC-FTIR: 3072, 2996, 2943, 1521, 1475, 1445,
1348, 1298, 1128, 991, 927, 787, 725 cm-1; MS [m/z (% rel. int.)]: 199(100, M+), 198(31), 184(6),
129(12), 104(21), 103(15), 77(10), 76(5); Found M+: 199.1108. Calc. for C12H13N3: 199.1110;
Analysis: Calc. for C12H13N3; C, 72.34; H, 6.58; N, 21.09 Found: C, 72.18; H, 6.44; N, 21.35;
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Compound 5: H-NMR (400 MHz, CD3OD): δ 2.44 (s, 3H), 4.76 (dt, J=6.7, 1.5 Hz, 2H), 5.16 (dd,
J=18.1, 0.9 Hz, 1H), 5.32 (dd, J=11.1, 0.8 Hz, 1H), 6.05 (ddt, J= 15.5, 10.3, 5.2 Hz, 1H), 7.47-7.49 (m,
3H), 7.63-7.64 (m, 2H) ppm; 13C-NMR (100 MHz, CD3OD): δ 13.9, 51.3, 118.3, 128.0, 128.6, 128.8,
130.1, 132.4, 160.3 ppm; GC-FTIR: 3075, 3040, 2995, 2945, 1506, 1456, 1413, 1381, 1338, 1288,
1248, 1182, 1016, 925, 805, 768 cm-1; MS [m/z (% rel. int.)]: 199(100, M+), 198(38), 184(6), 174(4),
159(4), 104(19), 77(10). Found M+: 199.1108 Calc. for C12H13N3: 199.1110
Trans 1-(2-Butenyl)-5-methyl-3-phenyl-1H-1,2,4-triazole (8) and trans-1-(2-butenyl)-3-methyl-5-
phenyl-1H-1,2,4-triazole (9).
Prepared from 6 (1.18 g, 7.40 mmol), sodium hydride (0.18 g, 7.40 mmol) and crotyl bromide (80 %
1
trans) (1.50 g, 11.10 mmol) in DMF (12 mL) yielding a 82:18 mixture of 8 and 9. Compound 8: H-
NMR (400 MHz, CDCl3): δ 1.70 (dd, J=6.4, 1.5 Hz, 3H), 2.46 (s, 3H), 4.66 (dd, J= 4.1, 1.5 Hz, 2H),
13
5.61-5.68 (m, 2H), 7.33-7.49 (m, 3H), 8.05-8.07 (m, 2H) ppm; C-NMR (100 MHz, CDCl3): δ 12.0,
13.1, 17.6, 45.6, 50.5, 123.9, 124.6, 126.1, 128.5, 128.6, 128.9, 129.9, 131.2, 152.4, 152.6, 160.6 ppm;
GC-FTIR: 3071, 3039, 2937, 2873, 1521, 1475, 1445, 1349, 1297, 1127, 965, 808, 782, 725 cm-1; MS
[m/z (% rel. int.)]: 213(100, M+), 212(4), 199(7), 198(36), 160(12), 159(100), 118(19), 104(27),
103(12), 77(12). Found M+: 213.1269 Calc. for C13H15N3: 213.1266; Analysis: Calc. for C13H15N3 ; C,
1
72.34; H, 6.58; N, 21.09 Found: C, 72.66; H, 6.87; N, 20.78. Compound 9: H-NMR (400 MHz,
CDCl3): δ 1.74 (d, J=4.9 Hz, 3H), 2.45 (s, 3H), 4.70 (d, J=3.4 Hz, 2H), 5.60-5.73 (m, 2H), 7.46-7.49
(m, 3H), 7.62-7.65 (m, 2H) ppm; 13C-NMR (100 MHz, CDCl3): δ 13.9, 17.8, 46.3, 50.8, 124.7, 125.2,
128.1, 128.5, 128.7, 130.0, 154.9, 160.1 ppm; GC-FTIR: 3073, 2945, 2872, 1504, 1458, 1412, 1380,
1340, 1242, 1017, 964, 811, 771, 725 cm-1; MS [m/z (% rel. int.)]: 213(73, M+), 212(9), 199(7),
198(54), 197(5), 172(5), 160(10), 159(100), 188(35), 104(26), 77(12). Found M+: 213.1269 Calc. for
C13H15N3: 213.1266; Analysis: Calc. for C13H15N3 ; C, 73.21; H, 7.09; N, 19.70. Found: C, 73.44; H,
6.78; N, 19.95.
1-Benzyl-5-methyl-3-phenyl-1H-1,2,4-triazole (13), and 1-benzyl-3-methyl-5-phenyl-1H-1,2,4-triazole,
(14).
Prepared from 6 (0.50 g, 3.14 mmol), sodium hydride (0.19 g, 7.85 mmol) and benzyl bromide (0.81 g,
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3.14 mmol) in DMF (8 mL) yielding a 90:10 mixture of 13 and 14. Compound 13: H-NMR (400
MHz, CD3OD): δ 2.45 (s, 3H), 5.40 (s, 2H), 7.24-7.27 (m, 3H), 7.31-7.44 (m, 5H), 7.98-8.00 (m, 2H)