OSTROGLYADOV et al.
630
procedure described in [5]. mp 160–162°C (from
MeOH); published data [5]: mp 160–161°C. IR spec-
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trum, ν, cm–1: 1375, 1555 (NO2). H NMR spectrum
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(DMSO-d6), δ, ppm: 5.83 m (1H, CHOH); 6.30 m
(2H, CHPh, OH); 7.20 m, 7.25 m, and 7.70 m (4H,
4-H, 5-H, 6-H, 7-H); 7.48 m and 7.60 m (5H, C6H5);
3.88 s (3H, NMe).
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1-Methyl-2-(2-nitro-2-phenylethenyl)-1H-benz-
imidazole (III). Acetic anhydride, 2.1 ml, was added
to 0.9 g (3 mmol) of nitro alcohol II, and the mixture
was heated for 30 min on a boiling water bath under
stirring until it became homogeneous. The mixture was
then treated with 16.5 ml of ice water under stirring
and was stirred for 2 h more. The precipitate was
filtered off and washed on a filter with water, alcohol,
and diethyl ether. Yield 0.7 g (83%), mp 210–212°C
(from MeOH); published data [5]: mp 160–161°C.
1H NMR spectrum (CDCl3), δ, ppm: 6.83 (1H, HA),
7.50 and 7.54 (5H, C6H5), 7.30 and 7.80 (4H, 4-H,
5-H, 6-H, 7-H), 3.88 (3H, Me). Found, %: C 68.53,
68.78; H 4.27, 4.50; N 15.42, 15.40. C16H13N3O2. Cal-
culated, %: C 68.82; H 4.66; N 15.05.
The 1H NMR spectra were recorded on a Jeol JNM
ECX400A spectrometer at 400 MHz. The IR spectra
were measured on an InfraLYuM FT-02 instrument
from samples dispersed in mineral oil. The electronic
absorption spectra were obtained on a Shimadzu UV-
2401 spectrophotometer from solutions in acetonitrile.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 4 2009