Synthesis and application of new S-benzoheterocycle…
Instrumentation
1H NMR and 13C NMR spectra were recorded in CDCl3 with a Bruker AVANCE III
600 MHz spectrometer. High-resolution mass spectra were obtained on a Thermo
Scientifc Q Exactive mass spectrometer. UV–Vis absorption spectra were recorded
in DMSO (1×10−5 M) on a Hitachi UH-5300 UV spectrophotometer (Hitachi High-
Technologies, Tokyo, Japan). The cured flms were performed on a UV-Curing
machine (ZB-T150-UV1000), and the hardness of flms was recorded by a portable
pencil scratch hardness tester (QHQ-A).
Synthesis
The substitution reaction of acyl chloride and mercapto reagent was carried out under
mild conditions, and the general procedure is as follows: Acyl chloride (2.0 mmol),
mercapto reagent (1.0 mmol) and base (2.0 mmol) were dissolved in THF. The reac-
tion mixture was stirred at 60 °C for 12 h. After cooling to room temperature, the pre-
cipitates were fltered of. The crude products were purifed by silica gel chromatog-
raphy using dichloromethane and petroleum ether as the eluent to aford compound 3.
S‑(1‑benzoyl‑6‑methoxy‑1H‑benzo[d]imidazol‑2‑yl) benzothioate 3e Pale yellow
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crystals (75%), mp: 152–156 °C. H NMR (600 MHz, CDCl3) δ 7.97–7.90 (m,
ArH, 4H), 7.66 (dd, J=16.3, 7.5 Hz, ArH, 2H), 7.55–7.48 (m, ArH, 4H), 7.33 (dd,
J=10.6, 5.7 Hz, ArH, 1H), 6.92 (d, J=2.4 Hz, ArH, 1H), 6.88 (dd, J=8.9, 2.4 Hz,
ArH, 1H), 3.85–3.79 (m, -OCH3,3H). 13C NMR (151 MHz, CDCl3) δ 170.15,
169.00, 168.92, 157.91, 134.62, 134.38, 132.48, 132.31, 132.26, 130.72, 130.63,
128.93, 128.83, 125.41, 112.85, 112.10, 97.07, 77.25, 77.04, 76.83, 55.98. HRMS
(ESI) m/z: calcd for C22H16N2O3S: 389.0915, found: 389.0950.
S‑(6‑methoxy‑1‑(4‑methylbenzoyl)‑1H‑benzo[d]imidaz1ol‑2‑yl) 4‑methylbenzothio‑
ate 3f Pale yellow crystals (76%), mp: 239–241 °C. H NMR (600 MHz, CDCl3)
δ 7.85 (dd, J=10.6, 8.3 Hz, ArH, 4H), 7.32 (t, J=7.4 Hz, ArH, 4H), 7.27–7.24
(d, J=8.7 Hz, ArH, 1H), 6.86 (dt, J=8.7, 2.2 Hz, ArH, 2H), 3.81 (s, OCH3, 3H),
2.50–2.40 (d, J=3.1 Hz, CH3, 6H). 13C NMR (151 MHz, CDCl3) δ 169.87, 168.66,
168.58, 157.79, 146.18, 145.90, 132.35, 131.08, 131.00, 129.73, 129.63, 129.58,
129.44, 125.57, 112.60, 111.95, 96.86, 55.97, 21.99, 21.97. HRMS (ESI) m/z: calcd
for C24H20N2O3S{[M+H]+}: 417.1195, found: 417.1262.
S‑(6‑nitro‑1H‑benzo[d]imidazol‑2‑yl) benzothioate 3g Colorless oil liquid (62%),
1H NMR (600 MHz, CDCl3) δ 8.22–8.17 (m, ArH, 3H), 7.71 (t, J=7.5 Hz, ArH,
2H), 7.56 (t, J=7.9 Hz, ArH, 4H).
S, S’‑(thiobis(4,1‑phenylene)) dibenzothioate 3h White Crystals (81%), mp:
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112–114 °C. H NMR (600 MHz, CDCl3) δ 8.05 (t, J=8.6 Hz, ArH, 2H), 7.64 (t,
J=7.3 Hz, ArH, 1H), 7.49 (d, ArH, 6H). 13C NMR (151 MHz, CDCl3) δ 189.86,
137.24, 136.47, 135.78, 133.83, 131.52, 128.82, 127.5, 126.45, 77.26, 77.05, 76.83.
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