1
TABLE 1. The Characteristics of the H NMR Spectra of Compounds 6a-f
and 8a-c
Com-
δ, ppm (DMSO-d6), J (Hz)
pound
7.04 (6Н, m, p- + m-С6Н5); 7.27 (6Н, m, о-С6Н5 + 5-, 6-Н); 7.70 (2Н, m, 4-, 7-Н);
13.09 (2Н, s, NH)
6а
6b
6c
7.07 (3H, m, p- + m-С6Н5); 7.32 (4H, m, о-С6Н5 + 5-, 6-Н); 7.50 (2H, m, m-C6H4NO2,
J = 8.7); 7.75 (2H, m, 4-, 7-Н); 7.88 (2H, m, o-C6H4NO2, J = 8.7); 13.10 (2Н, s, NH)
4.17 (2Н, s, СН2); 6.60 (2Н, d, о-ОС6Н5); 6.83 (1Н, m, p-ОС6Н5);
7.16 (2Н, m, m-ОС6Н5); 7.27 (2H, m, 5-, 6-Н); 7.46 (3H, m, p- + m-С6Н5);
7.63 (2H, d, о-С6Н5, J = 7.7 ); 13.07 (2Н, s, NH)
1.64 (3Н, s, СН3); 7.24 (2H, m, 5-, 6-Н); 7.47 (5Н, m, С6Н5); 7.67 (2Н, m, 4, 7-Н);
6d
6e
6f
13.09 (2Н, s, NH)
7.31 (2H, m, 5-, 6-Н); 7.49 (2H, m, m-С6Н5); 7.59 (1Н, m, p-С6Н5); 7.67 (2Н, m, 4-, 7-Н);
7.73 (2H, m, о-С6Н5, J = 7.4); 12.94 (2Н, s, NH)
7.30 (2H, m, 5-, 6-Н); 7.48 (5Н, m, С6Н5); 7.74 (2Н, m, 4-, 7-Н); 9.31 (1Н, s, СНО);
13.20 (2Н, s, NH)
7.15 (2H, m, 5-, 6-Н); 7.38 (2H, m, m-С6Н5); 7.46 (2Н, m, 4-, 7-Н); 7.56 (1H, m, p-С6Н5);
7.86 (2H, d, о-С6Н5, J = 7.5); 8.07 and 8.30 (1Н, 2s, 3'-H); 12.33 and 12.38 (1Н, 2s, 1-H);
13.34 and 13.50 (1Н, 2s, 1'-H); hydrochloride: 7.50 (3Н, m, p- + m-С6Н5);
7.54 (2H, m, 5-, 6-Н); 7.62 (2H, m, о-С6Н5); 7.75 (2Н, m, 4-, 7-Н); 8.57 (1Н, s, 3'-H);
NH not appears
8а
7.13 (2H, m, 5-, 6-Н); 7.25 (2H, m, о-С6Н5N); 7.37 (8Н, m, p- + m-С6Н5N+С6Н5);
8b
8c
7.48 (2Н, m, 4-, 7-Н); 8.35 (1Н, s, 3'-H); 12.40 (1Н, s, 1-H)
7.14 (2H, m, 5-, 6-Н); 7.45 (7Н, m, 4-, 7-Н + С6Н5); 7.49 (2H, d, o-C6H4NO2, J = 9.8);
8.23 (2H, d, m-C6H4NO2, J = 9.8); 8.47 (1Н, s, 3'-H); 12.46 (1Н, s, 1-H)
EXPERIMENTAL
The IR spectra were recorded on a UR-20 instrument for tablets with potassium bromide. The 1H NMR
spectra were obtained on a Varian VXR-300 spectrometer at 300 MHz with DMSO-d6 as solvent and TMS as
internal standard. The reactions and the individuality of the synthesized compounds were monitored by TLC on
Silufol UV-254 plates in the 9:1 benzene–ethanol solvent system (development in UV light).
p
A mixture of compound
2-(Benzoyl- -nitrobenzoylmethylene)-2,3-dihydro-1H-benzimidazole (6b).
2 (8.88 g, 20 mmol) and acid 3b (3.34 g, 20 mmol) in anhydrous dioxane (10 ml) was boiled for 4 h. After
cooling the mixture was mixed with water (50 ml). The aqueous layer was decanted. The residue was boiled
with 2-propanol (30 ml) until crystallization began. After cooling the precipitate was filtered off and washed
with 2-propanol. Yield 6.51 g (84%); mp 248.5-250°C (n-butanol–DMF, 3:1). IR spectrum, , cm-1: 1350, 1540
ν
(NO2), 1595, 1615 (C=C and C=O), 3275 (NH). Found, %: C 68.7; H 4.0; N 10.8. C22H15N3O4. Calculated, %:
C 68.6; H 3.9; N 10.9.
2-(Benzoylphenoxyacetylmethylene)-2,3-dihydro-1H-benzimidazole (6c). A mixture of compound 2
(0.44 g, 1 mmol), acid 3c (0.23 g, 1.5 mmol), and anhydrous dioxane (1 ml) was boiled for 3 h. To the boiling
solution we added water (0.5 ml). After cooling the precipitate was filtered off and washed with 2-propanol.
Yield 0.22 g (59%); mp 216.5-218°C (aqueous dioxane, 1:2). IR spectrum, , cm-1: 1595, 1615 (C=C and C=O),
ν
3255 (NH). Found, %: C 74.7; H 4.8; N 7.6. C22H15N3O4. Calculated, %: C 74.6; H 4.9; N 7.6.
2-(Acetylbenzoylmethylene)-2,3-dihydro-1H-benzimidazole (6d). A. A mixture of compound 2
(2.22 g, 5 mmol) and acid 3d (4.2 ml, 70 mmol) was kept at 95-100°C for 45 min. After cooling the mixture was
stirred with 2-propanol (4.0 ml). The precipitate was filtered off and washed with 2-propanol. Yield 1.18 g
(85%); mp 273.5-275°C (o-xylene). IR spectrum, , cm-1: 1600, 1615 (C=C and C=O), 3215 (NH). Found, %:
ν
C 73.5; H 5.1; N 10.0. C22H15N3O4. Calculated, %: C 73.4; H 5.1; N 10.0.
557