3360, 2726, 1693, 1569 cm-1. m/z 255 (M + H)+. Anal. Calcd for C14H10N2O3: C, 66.14; H, 3.96; N,
11.02. Found: C, 66.09; H, 3.98; N, 11.05.
4.2.1.3. 2-(3-Hydroxyphenyl)-1H-benzo[d]imidazole-5-sulfonic acid (11). Yield 69%. Mp 219-220 °C
(EtOH). 1H NMR (DMSO-d6): δ 7.16 (d, J = 8.0 Hz, 1H, Ar), 7.53 (d, J = 8.0 Hz, 1H, Ar), 7.57 (s, 1H, Ar),
7.62 (d, J = 8.0 Hz, 1H, Ar), 7.77 (d, J = 8.0 Hz, 1H, Ar), 7.82 (d, J = 8.5 Hz, 1H, Ar), 9.96 (s, 1H, Ar),
10.23 (s, 1H, OH). IR (Nujol) 3397, 3274, 1631, 1588 cm-1. m/z 291 (M + H)+. Anal. Calcd for
C13H10N2O4S: C, 53.79; H, 3.47; N, 9.65. Found: C, 53.84; H, 3.46; N, 9.68.
4.2.1.4. 2-(2,4-Dihydroxyphenyl)-1H-benzo[d]imidazole-5-carbonitrile (12). Yield 63%. Mp 233-234
°C (EtOH). 1H NMR (DMSO-d6): δ 6.56 (d, J = 8.5 Hz, 1H, Ar), 6.68 (s, 1H, Ar), 7.81 (d, J = 8.0 Hz, 1H,
BIM), 7.89 (d, J = 8.0 Hz, 1H, BIM), 8.05 (d, J = 8.5 Hz, 1H, Ar), 8.20 (s, 1H, BIM). IR (Nujol) 3348, 3211,
3086, 2242, 1611 cm-1. m/z 252 (M + H)+. Anal. Calcd for C14H9N3O2: C, 66.93; H, 3.61; N, 16.73.
Found: C, 66.99; H, 3.60; N, 16.70.
4.2.1.5. 2-(2,5-Dihydroxyphenyl)-1H-benzo[d]imidazole-5-carbonitrile (13). Yield 78%. Mp >250 °C
(EtOH). 1H NMR (DMSO-d6): δ 6.98 (s, 2H, Ar), 7.50 (s, 1H, Ar), 7.73 (d, J = 8.0 Hz, 1H, BIM), 7.86 (d,
J = 8.5 Hz, 1H, BIM), 8.21 (s, 1H, BIM). 13C (DMSO-d6): δ 108.2, 112.6, 116.6, 121.1 (2C), 125.6 (2C),
128.9, 130.3, 135.7, 138.9, 141.8, 147.1, 148.1. IR (Nujol) 2230, 1617, 1564 cm-1. m/z 252 (M + H)+.
Anal. Calcd for C14H9N3O2: C, 66.93; H, 3.61; N, 16.73. Found: C, 66.87; H, 3.63; N, 16.77.
4.2.1.6. 2-(2,5-Dihydroxyphenyl)-1H-benzo[d]imidazole-5-carboxylic acid (14). Yield 65%. Mp >250
°C (EtOH). 1H NMR (DMSO-d6): δ 6.99 (s, 2H, Ar), 7.47 (s, 1H, Ar), 7.81 (d, J = 8.0Hz, 1H, BIM), 7.99
(d, J = 8.5Hz, 1H, BIM), 8.31 (s, 1H, BIM), 9.40 brs (1H, OH); 13C (DMSO-d6): δ 113.2, 116.4 (2C), 119.8
(2C), 120.5 (2C), 132.7, 139.2, 142.6, 145.7 , 152.0, 154.2, 153.9. IR (Nujol) 31.84, 2720, 1718, 1620
cm-1. m/z 271 (M + H)+. Anal. Calcd for C14H10N2O4: C, 62.22; H, 3.73; N, 10.37. Found: C, 62.28; H,
3.71; N, 10.34.
4.2.1.7. 2-(2,5-Dihydroxyphenyl)-1H-benzo[d]imidazole-5-sulfonic acid (15). Yield 71%. Mp >250 °C
(EtOH). 1H NMR (DMSO-d6): δ 7.04 (s, 2H, Ar), 7.43 (s, 1H, Ar), 7.75 (s, 2H, Ar), 8.02 (s, 1H, Ar), 9.41
(s, 1H, NH). IR (Nujol) 3392, 3225, 3097, 1633, 1569 cm-1. m/z 307 (M + H)+. Anal. Calcd for
C13H10N2O5S: C, 50.98; H, 3.29; N, 9.15. Found: C, 50.94; H, 3.31; N, 9.18.
4.2.1.8. 2-(3,4-Dihydroxyphenyl)-1H-benzo[d]imidazole-5-carbonitrile (16). Yield 75%. Mp >250 °C
(EtOH). 1H NMR (DMSO-d6): δ 7.04 (d, J = 8.5 Hz, 1H, Ar), 7.65 (s, 1H, Ar), 7.67 (d, J = 8. 5 Hz, 1H, Ar),
7.79 (d, J = 8.5 Hz, 1H, BIM), 7.85 (d, J = 8.0 Hz, 1H, BIM), 8.21 (s, 1H, BIM). IR (Nujol) 3428, 3331,
3105, 2242, 1611 cm-1. m/z 252 (M + H)+. Anal. Calcd for C14H9N3O2: C, 66.93; H, 3.61; N, 16.73.
Found: C, 66.85; H, 3.59; N, 16.70.