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Ferric nitrate, hydrogen peroxide
(30%) as well as all the aromatic aldehydes, 1,2-phenylenediamine
derivatives and 2-aminothiophenol employed as substrates are commer-cially
available and were used without further purification. The concentration
of the commercial 30% H2O2 solution was
checked iodometrically prior to use.
General
procedure for the Synthesis of Benzimidazoles and Benzothiazoles:
A mixture of 1,2-phenylenediamine (1 mmol), aryl aldehyde (1 mmol),
H2O2 (30%, 4 mmol, 0.4 mL) and Fe(NO3)3˙9
H2O (0.1 mmol, 0.04 g) was heated at 50 ˚C for
the appropriate time as mentioned in Table 2. After completion of
the reaction, the reaction mixture was dissolved in EtOH (10 mL)
and then poured into ice-water (30 mL). The pure solid product was
filtered, washed with ice-water and subsequently dried. An identical
procedure was employed using 2-aminothiophenol (1 mmol), aryl aldehyde
(1 mmol) in the presence of 30% H2O2 (4
mmol) and Fe(NO3)3.9 H2O (0.1 mmol)
for the synthesis of benzothiazoles (Table 4).
Spectroscopic and Physical Data for Selected Compounds:
2-Phenyl-1
H
-benzimidazole: mp 290-291 ˚C
(lit.
[¹8]
292 ˚C). ¹H
NMR (200 MHz, DMSO-d
6): δ = 7.19-7.23
(m, 2 H), 7.51-7.61 (m, 5 H), 8.16-8.21 (m, 2
H), 12.91 (br, 1 H, NH). ¹³C NMR (50
MHz, DMSO-d
6): δ = 120.1,
123.0, 127.0, 127.3, 129.8, 130.8, 131.0, 152.1.
2-(2-Chlorophenyl)-1
H
-benzimidazole: mp 232-234 ˚C (lit.
[¹8]
234 ˚C). ¹H
NMR (200 MHz, DMSO-d
6): δ = 7.26-7.32
(m, 2 H), 7.56-7.73 (m, 5 H), 7.93-7.96 (m, 1
H), 12.78 (br, 1 H, NH). ¹³C NMR (50
MHz, DMSO-d
6): δ = 112.1, 119.4,
122.1, 123.1, 127.8, 130.3, 130.7, 131.6, 132.4, 149.4.
2-(4-Hydroxyphenyl)-1
H
-benzimidazole: mp 276-278 ˚C (lit.
[²5]
279 ˚C). ¹H
NMR (200 MHz, DMSO-d
6): δ = 5.04
(br, 1 H, OH), 6.91 (d, J = 8.7
Hz, 2 H), 7.12-7.21 (m, 2 H), 7.48-7.57 (m, 2
H), 7.97 (d, J = 8.7 Hz, 2 H),
10.02 (br, 1 H, NH). ¹³C NMR (50 MHz,
DMSO-d
6): δ = 120.1,
121.4, 125.9, 127.6, 133.9, 144.2, 157.2, 165.
2-(3-Bromophenyl)benzothiazole: mp 91-93 ˚C. ¹H
NMR (200 MHz, DMSO-d
6): δ = 7.34-7.66
(m, 4 H), 7.91-8.12 (m, 3 H), 8.29-8.31 (m, 1
H). ¹³C NMR (50 MHz, DMSO-d
6): δ = 122.1,
123.5, 123.8, 126, 126.6, 126.9, 130.6, 130.9, 134.2, 135.4, 135.8,
154.3, 166.5. Anal. Calcd for C13H8NSBr: C,
53.81; H, 2.70; N, 4.83; S, 11.05. Found: C, 54.00; H, 2.70; N,
5.20; S, 11.10.
2-(4-Formylphenyl)benzothiazole:
mp 135-136 ˚C. ¹H NMR (200
MHz, DMSO-d
6): δ = 7.39-7.56
(m, 2 H), 7.90-8.26 (m, 6 H), 10.06 (s, 1 H).¹³C
NMR (50 MHz, DMSO-d
6): δ = 122.2,
124.1, 126.0, 126.3, 127.1, 128.4, 130.7, 135.8, 138.0, 139.1, 154.5,
191.9. Anal. Calcd for C14H9NSO: C, 70.27;
H, 3.79; N, 5.85; S, 13.41. Found: C, 70.00; H, 3.70; N, 6.10; S,
13.20.
2-(4-Methylphenyl)benzothiazole:
mp 85-86 ˚C (lit.
[²6]
85-86 ˚C). ¹H
NMR (200 MHz, DMSO-d
6): δ = 2.41
(s, 3 H), 7.24-7.48 (m, 4 H), 7.86-8.04 (m, 4
H). ¹³C NMR (50 MHz, DMSO-d
6): δ = 22.0,
122.0, 123.5, 125.5, 126.7, 127.9, 130.2, 131.3, 135.4, 141.9, 154.6,
168.7.
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