3,5-DIARYL-1,2,4-THIADIAZOLES
2937
186.9, 172.5, 135.5, 134.8, 134.3, 132.1, 132.0, 130.6, 130.0, 128.5, 127.3, 126.4, 125.7.
Anal. calcd. for C14H8Cl2N2S: C, 54.74; H, 2.62; N, 9.12; S, 10.44. Found: C, 54.60;
H, 2.51; N, 9.10; S, 10.61.
3,5-Bis(4-chlorophenyl)-1,2,4-thiadiazole 3h. White crystals; 1H NMR
(500 MHz, CDCl3) 8.32 (d, J ¼ 8.6 Hz, 2H), 8.99 (d, J ¼ 8.5 Hz, 2H), 7.51 (d,
J ¼ 8.5 Hz, 2H), 7.48 (d, J ¼ 8.6 Hz, 2H).
3,5-Bis(4-fluorophenyl)-1,2,4-thiadiazole 3i. White crystals; 1H NMR
(500 MHz, CDCl3) 8.38 (dd, J ¼ 12.2, 6.7 Hz, 2H), 8.05 (dd, J ¼ 12.2, 6.7 Hz, 2H),
7.16–7.24 (m, 4H); 13C NMR (125 MHz, CDCl3) 187.0, 172.8, 166.0, 165.2, 163.9,
163.2, 130.4, 129.6, 116.5, 115.7. Anal. calcd. for C14H8F2N2S: C, 61.30; H, 2.94;
N, 10.21; S, 11.69. Found: C, 61.21; H, 2.80; N, 10.02; S 11.80.
3,5-Bis(4-methoxyphenyl)-1,2,4-thiadiazole 3j. Pale yellow needles; 1H
NMR (500 MHz, CDCl3) 8.33 (d, J ¼ 6.9 Hz, 2H), 7.99 (d, J ¼ 6.9 Hz, 2H),
7.00–7.03 (m, 4H), 3.90 (s, 3H), 3.89 (s, 3H).
3,5-Bis(2,4-dichlorophenyl)-1,2,4-thiadiazole 3k. White needles; 1H NMR
(500 MHz, CDCl3) 8.57 (d, J ¼ 8.7 Hz, 1H), 8.04 (d, J ¼ 8.4 Hz, 1H), (d, J ¼ 2.1 Hz,
1H), (d, J ¼ 2.1 Hz, 1H), (dd, J ¼ 8.7, 2.1 Hz, 1H), (dd, J ¼ 8.4, 2.1 Hz, 1H); 13C
NMR (125 MHz, CDCl3) 182.3, 173.2, 138.0, 136.4, 136.3, 134.4, 134.2, 133.1,
131.4, 130.8, 130.3, 120.7, 128.1, 127.2. Anal. calcd. for C14H6Cl4N2S: C, 44.71;
H, 1.61; Cl, 37.71; N, 7.45; S, 8.53 Found: C, 44.60; H, 1.54; N, 7.37; S,8.74 .
1
3,5-Di(furan-2-yl)-1,2,4-thiadiazole 3l. White needles; H NMR (500 MHz,
CDCl3) 7.94 (d, J ¼ 3.6 Hz, 1H), 7.70 (d, J ¼ 3.7 Hz, 1H), 7.59 (d, J ¼ 5.1 Hz, 1H),
7.46 (d, J ¼ 5.0 Hz, 1H), 7.13–7.22 (m, 2H).
ACKNOWLEDGMENT
We are grateful to the University of Isfahan Research Council for financial
support of this work.
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