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139.1, 138.1, 131.1 (Ar-C), 128.5 (Ar-2CH-m), 128.3, 128.2 (Ar-2CH-o,m’), 128.1 (Ar-
CH-p,p’), 127.9 (Ar-2CH-o’), 127.2 (Ar-CH-p, p’), 101.0 (thiazole-C-5), 24.3, 18.7 (CH3).
15N (NMR, DMSO-d6): δ = 344.5 (azomethine-N), 138.5 (thiazole-N). Anal. Calcd. For
C18H17N3S (307.42): C, 70.33; H, 5.57; N, 13.67. Found: C, 70.22; H, 5.45; N, 13.55.
(Z)-3,4-Diphenyl-2-((E)-1-phenylethylidene)hydrazono)-2,3-dihydrothiazole (6b). Pale
yellow crystals (EtOH), yield: 0.350 g (95%), Rf = 0.4 (Toluene: AcOEt; 10:1), m.p.
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310–312°C (m.p. [25] 310–312°C). H NMR (400 MHz, DMSO-d6): δ = 7.81 (dd, 2H,
J = 8.0, 1.50 Hz, Ar-H-o), 7.38–7.36 (m, 5H, Ar-H-m, m’’,p’’), 7.32–7.29 (m, 3H, Ar-H-
o,p/p’), 7.27–7.25 (m, 3H, Ar-H- H-m’, p’/p), 7.21–7.20 (m, 2H, Ar-H- H-o’), 6.66 (s, 1H,
H-5), 2.20 (s, 3H, CH3), 13C NMR (400 MHz, DMSO-d6): δ = 168.9 (C-2), 155.8, 139.6,
138.3, 137.7, 130.8 (Ar-C), 128.9 (Ar-CH-p’’), 128.7, 128.4 (Ar-2CH-o’), 128.3 (Ar-CH-
p,p’), 128.2 (Ar-2CH-m’), 128.1 (Ar-2CH-m’’), 128.0 (Ar-2CH-o’), 127.6 (Ar-CH-p,p’),
125.9 (Ar-2CH-o’), 102.0 (thiazole-C-5), 14.4 (CH3). 15N (NMR, DMSO-d6): δ = 354.1
(azomethine-N), 142.6 (thiazole-N). Anal. calcd. for C23H19N3S (369.49): C, 74.77; H,
5.18; N, 11.37. Found: C, 74.62; H, 5.00; N, 11.25.
(Z)-3-Allyl-4-phenyl-2-(E)-1-phenylethylidene)hydrazono)-2,3-dihydrothiazole (6c).
Pale yellow crystals (CH3CN), yield: 0.310 g (93%), Rf = 0.45 (Toluene: AcOEt; 10:1),
m.p. 247–249°C (m.p. [25] 246–248°C). 1 H NMR (400 MHz, DMSO-d6): δ = 7.54–7.44
(m, 4H, Ar-CH), 7.34–7.21 (m, 6H, Ar-CH), 7.12 (s, 1H, H-5), 5.65–5.63 (m, 1H, allyl-
CH), 5.28–5.24 (m, 2H, allyl-CH2-), 4.49 (br, 2H, allyl-CH2N), 2.31 (s, 3H, CH3); 13C
NMR (100 MHz, DMSO-d6): δ = 163.0 (thiazole-C), 158.9, 142.2, 137.9, 141.5 (Ar-C),
135.7 (Allyl-CH), 130.2, 129.2, 128.9, 128.2, 127.8, 126.7 (Ar-CH), 116.7 (Ally-CH2), 106.2
(thiazole-CH-5), 45.8 (Allyl-CH2N), 14.44 (CH3); Anal. calcd. for C20H19N3S (333.45): C,
72.04; H, 5.74; N, 12.60. Found: C, 72.16; H, 5.80; N, 12.46.
(Z)-3-Ethyl-4-phenyl-2-propan-2-ylidene)hydrazono)-2,3-dihydrothiazole (6d). Pale
yellow crystals (CH3OH), yield: 0.202 g (78%), m.p. =97–98°C (lit [25] 96°C). 1H NMR
(400 MHz, CDCl3): δ = 7.78–7.76 (m, 2H, Ph-H), 7.50-.46 (m, 3H, Ph-H), 7.10 (s, 1H,
thiazole-5), 4.00 (q, 2H, J = 7.0 Hz, CH2-ethyl), 2.40 (s, 3H, CH3), 1.98 (s, 3H, CH3), 1.20
(t, 3H, J = 7.0 Hz, CH3-ethyl). 13C NMR (400 MHz, CDCl3): δ = 168.0, 158.0 (C = N),
139.4 (C-4-thiazole), 136.5 (Ph-C), 128.6, 127.0 (Ph-2CH), 126.0 (Ph-CH), 103.0 (thiazole-
CH-5), 39.4 (CH2-ethyl), 22.4, 21.0 (CH3), 13.0 (CH3-ethyl). Anal. calcd. for C14H17N3S
(259.37): C, 64.83; H, 6.61; N, 16.20. Found: C, 64.70; H, 6.81; N, 16.36.
(Z)-3-Ethyl-4-phenyl-2-(E)-1-phenylethylidene)hydrazono)-2,3-dihydrothiazole (6e).
Pale yellow crystals (CH3OH), yield: 0.302 g (94%), Rf = 0.3 (Toluene: AcOEt; 10:1),
m.p. = 212–214 °C. 1H NMR (400 MHz, CDCl3): δ = 7.80–7.78 (m, 2H, Ph-H), 7.60–7.40
(m, 4H, Ph-H), 6.92 (s, 1H, thiazole-5), 6.86–6.82 (m, 4H, Ph-H), 4.00 (q, 2H, J = 7.0 Hz,
CH2-ethyl), 2.40 (s, 3H, CH3), 1.20 (t, 3H, J = 7.0 Hz, CH3-ethyl). 13C NMR (400 MHz,
CDCl3): δ = 164.0, 155.0 (C = N), 139.0 (C-4-thiazole), 137.0 (Ph-2C), 132.0, 131.0,
130.6, 130.0 (Ph-2CH), 127.0, 126.2 (Ph-CH), 102.0 (Thiazole-CH-5), 38.9 (CH2-ethyl),
21.0, 13.0 (CH3). Anal. calcd. for C19H19N3S (321.44): C, 71,00; H, 5.96; N, 13.07. Found:
C, 71.10; H, 6.00; N, 13.12.
Acknowledgements
The NMR spectrometer at Florida Institute of Technology was purchased with assistance from the
U.S. National Science Foundation (CHE 03-42251).