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F. Ke et al.
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(12) Benzimidazoles 2a–w; General Procedure
A 10 mL glass tube was charged with the appropriate 2-haloan-
iline (0.5 mmol), 25–28% aq NH3 (2 mL), the appropriate alde-
hyde (0.6 mmol), NiCl2 (11.88 mg, 0.05 mmol), quinolin-8-ol
(7.258 mg, 0.05 mmol), and Cs2CO3 (325.82 mg, 1.0 mmol). The
vessel was then sealed with a septum and placed in the cavity of
a Discover microwave synthesizer (CEM Corp., Buckingham,
UK), and irradiated at 130 W. The temperature was ramped
from r.t. to the desired temperature of 100 °C, then held at this
temperature for 13 min. The mixture was stirred continuously
during the reaction. The mixture was then allowed to cool to r.t.
and the solvent was removed under reduced pressure. The
residue was purified by column chromatography (silica gel) to
afford the corresponding product. The structures of the prod-
ucts were confirmed by NMR and MS spectroscopic analyses.
2-Phenyl-1H-benzo[d]imidazole (2a)
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Light-yellow solid; yield: 89.24 mg (92%). 1H NMR (400 MHz,
MeCN-d3): δ = 7.26–7.28 (m, 2 H), 7.55–7.64 (m, 5 H), 8.13 (d,
J = 4.0 Hz, 2 H), 10.96 (s, 1 H). 13C NMR (100 MHz, DMSO-d6):
δ = 151.70, 144.29, 135.48, 130.65, 130.30, 129.42, 126.91,
123.00, 122.14, 119.35, 111.79. ESI-MS: m/z = 195.1 [M + H]+.
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© Georg Thieme Verlag Stuttgart · New York — Synlett 2018, 29, A–E