2-Benzimidazolthiones
5
5-Methyl-2-benzimidazolthione (2c). Mp 292–294ꢁC, lit.16 mp 296ꢁC; IR (KBr, cmꢀ1
vmax 3156, 3125, 2987, 1557, 1514, 1467; H NMR (500 MHz, DMSO-d6) d 12.41 (s,
1H), 7. 03 – 6.92 (m, 3H), 2.33 (s, 3H). 13C NMR (126 MHz, DMSO-d6) d 168.24,
132.94, 132.12, 130.67, 123.66, 110.07, 109.58.
)
1
4-Methyl-2-benzimidazolthione (2d). Mp >300ꢁC, lit.18 mp >300ꢁC; IR (KBr, cmꢀ1
vmax 3155, 3121, 2989, 1559, 1516, 1468; H NMR (500 MHz, DMSO-d6) d 12.54 (d,
J ¼ 63.4 Hz, 2H), 7.03–6.90 (m, 3H), 2.37 (s, 3H). 13C NMR (126 MHz, DMSO-d6) d
168.40, 132.39, 131.99, 123.63, 122.81, 120.16, 107.38, 16.71.
)
1
4,5-Dimethyl-2-benzimidazolthione (2e). Mp 227–228ꢁC, lit.19 mp 225ꢁC; IR (KBr,
1
cmꢀ1) vmax 3275, 3134, 2988, 1626, 1432; H NMR (500 MHz, DMSO-d6) d 12.28 (s,
2H), 6.93 (s, 2H), 2.23 (s, 6H). 13C NMR (126 MHz, DMSO-d6) d 167.71, 131.07,
130.93, 110.50, 20.01.
5-Fluoro-2-benzimidazolthione (2f). Mp 277-278ꢁC, lit.20 mp 280ꢁC; IR (KBr, cmꢀ1
)
vmax 3160, 3087, 2986, 1633, 1434; 1H NMR (500 MHz, DMSO-d6) d 12.63 (d,
J ¼ 15.7 Hz, 2H), 7.14-6.95 (m, 3H). 13C NMR (126 MHz, DMSO-d6) d 169.80, 159.00
(d, J ¼ 236.6 Hz), 133.22 (d, J ¼ 13.1 Hz), 110.51 (d, J ¼ 9.9 Hz), 109.73 (d,
J ¼ 24.8 Hz), 97.33 (d, J ¼ 27.9 Hz).
5-Chloro-2-benzimidazolthione (2g). Mp >300ꢁC, lit.21 mp >300ꢁC; IR (KBr, cmꢀ1
)
vmax 3186, 3063, 2987, 1636, 1435; 1H NMR (500 MHz, DMSO-d6) d 12.65 (d,
J ¼ 12.6 Hz, 2H), 7.16 – 7.13 (m, 3H). 13C NMR (126 MHz, DMSO-d6) d 169.83,
133.72, 131.73, 127.16, 122.67, 110.98, 109.64.
5-Bromo-2-benzimidazolthione (2h). Mp 288-289ꢁC, lit.22 mp 289–292ꢁC; IR (KBr,
1
cmꢀ1) vmax 3201, 3069, 2987, 1634, 1436; H NMR (500 MHz, DMSO-d6) d 12.64 (d,
J ¼ 18.5 Hz, 2H), 7.66–6.73 (m, 2H). 13C NMR (126 MHz, DMSO-d6) d 169.69,
134.13, 132.09, 125.40, 114.77, 112.38, 111.46.
5-Nitro-2-benzimidazolthione (2i). Mp 269-271ꢁC, lit.22 mp 272ꢁC; IR (KBr, cmꢀ1
)
vmax 3235, 3101, 2988, 1645, 1457; 1H NMR (500 MHz, DMSO-d6) d 13.07 (d,
J ¼ 46.1 Hz, 2H), 8.08–8.05 (m, 1H), 7.88-7.85 (m, 1H), 7.30 – 7.25 (m, 1H). 13C
NMR (126 MHz, DMSO-d6) d 172.29, 143.06, 137.82, 132.70, 119.33, 109.63, 105.07.
1H,3H-Perimidin-2-thione (2j). Mp >300ꢁC, lit.16 mp >300ꢁC; IR (KBr, cmꢀ1) vmax
3213, 3167, 2981, 1637, 1447; 1H NMR (500 MHz, DMSO-d6) d 11.39 (s, 2H),
7.25–6.15 (m, 4H), 6.63 (d, J ¼ 7.3 Hz, 2H). 13C NMR (126 MHz, DMSO-d6) d 173.34,
135.73, 134.44, 128.74, 119.48, 116.54, 105.04.
5-Benzoyl-2-benzimidazolthione (2k). Mp 255-257ꢁC, lit.23 mp 254-256ꢁC; IR (KBr,
cmꢀ1) vmax 3202, 2988, 1640, 1454; 1H NMR (500 MHz, DMSO-d6) d 12.85 (d,
J ¼ 65.9 Hz, 2H), 7.72–7.27 (m, 8H). 13C NMR (126 MHz, DMSO-d6) d 195.45,
170.80, 138.26, 136.30, 132.69, 132.66, 131.49, 129.82, 128.94, 125.84,
111.30, 109.60.
2-Benzothiazolthione (2l). Mp 187-189ꢁC, lit.24 mp189-190ꢁC; IR (KBr, cmꢀ1) vmax
1
3158, 2989, 1562, 1488; H NMR (500 MHz, DMSO-d6) d 13.73 (s, 1H), 7.70–7.64
(m, 1H), 7.42-7.26 (m, 3H). 13C NMR (126 MHz, DMSO-d6) d 190.31, 141.73, 129.83,
127.61, 124.66, 122.22, 112.89.