1758
BAGAUTDINOVA et al.
119.35, 120.98, 129.31, 133.82, 133.96, 138.65, 143.47,
1.20–1.40 m (4Н, CH ), 1.62–1.77 m (2Н, CH ), 2.37 d
2 2
1
48.48, 153.33, 159.03. Mass spectrum (MALDI-TOF),
(3Н, СН , J = 4.3), 2.86 t (2Н, CH , J = 7.7), 4.34 s (2Н,
CH ), 5.25 s (1Н, OH), 5.47 d (2Н, CH O, J = 7.3), 7.03 t
2 2
3 2
+
m/z: 258 [M + Н] . Found, %: C 65.00; H 6.21; N 16.31.
C H N O . Calculated, %: C 65.34; H 5.89; N 16.33.
(1Н, Ph, J = 7.5), 7.07 t (1Н, Ph, J = 7.4), 7.23 d (1H, Ph,
J = 8.1), 7.51 d (1H, Ph, J = 7.9), 7.99 s (1Н, CH ), 9.03 s
14
15
3
2
General procedure for the preparation of benz-
imidazoles 5а–5f. Amixture of 1.2 mmol of monoimine
and 1.2 mmol of the corresponding aliphatic aldehyde
Py
1
3
(
1Н, OH). С NMR spectrum (DMSO-d ), δ , ppm:
6 C
1
4.35, 20.40, 22.37, 27.17, 27.32, 31.53, 39.49, 59.23,
3
110.76, 118.77, 121.37, 121.71, 128.93, 134.68, 135.74,
in 10 mL of ethanol was refluxed for 6 h. After cooling,
the solvent was partially removed in vacuum, and then
1
40.10, 142.75, 146.64, 149.93, 156.38. Mass spectrum
+
(MALDI-TOF), m/z: 340 [М + Н] . Found, %: С 70.45;
1
0 mL of diethyl ether was added to the residue. The
Н 7.66; N 11.81. С Н N O . Calculated, %: С 70.76;
precipitate was separated, washed with diethyl ether and
dried under vacuum.
20 25
3
2
Н 7.44; N 12.08.
-{(2-Hexyl-1H-benzo[d]imidazol-1-yl)methyl}-5-
hydroxymethyl)-2-methylpyridine-3-ol (5d). Yield
.29 g (71%), mp 193–195°С. IR spectrum (KBr), ν,
4
4
-{(2-Ethyl-1H-benzo[d]imidazol-1-yl)methyl}-5-
hydroxymethyl)-2-methylpyridine-3-ol (5a). Yield
.31 g (88%), mp 246–247°С. IR spectrum (KBr), ν,
(
(
0
0
–
1
1
–
1
1
cm : 1612 (С=N), 3170 (ОН). Н NMR spectrum
cm : 1615 (С=N), 3186 (ОН). Н NMR spectrum
(
DMSO-d ), δ, ppm (J, Hz): 0.86 t (3Н, CH , J = 6.8),
(
DMSO-d ), δ, ppm (J, Hz): 1.30 t (3Н, CH J = 7.5),
6
3
6
3
1
1
.21–1.30 m (4Н, CH ), 1.32 q (2Н, CH , J = 7.2),
2 2
2
.37 s (3Н, СН ), 2.92 q (2Н, CH , J = 7.5), 4.38 s (2Н,
3
2
.61–1.72 m (2Н, CH ), 2.37 d (3Н, СН , J = 4.3), 2.86 t
CH ), 5.27 s (1Н, OH), 5.46 s (2Н, CH O), 7.02 d. t (1Н,
2
3
2
2
(
2Н, CH , J = 7.7), 4.34 s (2Н, CH ), 5.23 s (1Н, OH),
Ph, J = 7.5, 1.3), 7.08 d. t (1H, Ph, J = 7.5, 1.3), 7.19 d
1H, Ph, J = 7.8), 7.53 d (1H, Ph, J = 7.8), 8.00 s (1Н,
2
2
5
.46 s (2Н, CH O), 7.03 t (1Н, Ph, J = 7.6), 7.07 t (1Н,
2
(
13
Ph, J = 7.5), 7.23 d (1H, Ph, J = 8.0), 7.51 d (1H, Ph,
CH ), 9.02 s (1Н, OH). С NMR spectrum (DMSO-d ),
Py
6
13
J = 7.8), 7.98 s (1Н, CH ), 9.00 s (1Н, OH). С NMR
δ, ppm: 11.89, 20.38, 20.76, 39.50, 59.22, 110,69, 118.77,
Py
1
1
21.30, 121.71, 128.89, 134.60, 135.77, 140.15, 142.70,
spectrum (DMSO-d6), δC, ppm: 14.42, 20.41, 22.52,
27.37, 27.46, 29.01, 31.51, 39.49, 59.24, 110.76, 118.77,
121.37, 121.71, 128.93, 134.69, 135.76, 140.08, 142.76,
146.64, 149.96, 156.38. Mass spectrum (MALDI-TOF),
46.64, 149.99, 157.23. Mass spectrum (MALDI-TOF),
+
m/z: 298 [М + Н] . Found, %: С 68.45; Н 6.66; N 14.81.
С Н N O . Calculated, %: С 68.65; Н 6.45; N 14.13.
17
19
3
2
+
m/z: 354 [М + Н] . Found, %: С 71.45; Н 7.66; N 11.81.
5
-(Hydroxymethyl)-2-methyl-4-{(2-propyl-1H-
С Н N O . Calculated, %: С 71.34; Н 7.71; N 11.89.
benzo[d]imidazol-1-yl)methyl}pyridine-3-ol (5b).
Yield 0.29 g (81%), mp 209–211°С. IR spectrum (KBr),
ν, cm : 1615 (С=N), 3167 (ОН). Н NMR spectrum
21 27
3
2
4-{(2-Heptyl-1H-benzo[d]imidazol-1-yl)methyl}-
5-(hydroxymethyl)-2-methylpyridine-3-ol (5e). Yield
–
1
1
–1
(DMSO-d ), δ, ppm (J, Hz): 0.95 t (3Н, CH , J = 7.4),
0.40 g (93%), mp 155–158°С. IR spectrum (KBr), ν, cm :
6
3
1
1
.74 q (2Н, CH , J = 7.4), 2.37 s (3Н, СН ), 2.87 t (2Н,
1614 (С=N), 3054 (ОН). Н NMR spectrum (DMSO-d ),
2
3
6
CH , J = 7.7), 4.36 s (2Н, CH ), 5.26 s (1Н, OH), 5.46 s
δ, ppm (J, Hz): 0.86 t (3Н, CH , J = 6.8), 1.21–1.30 m
2
2
3
(
2Н, CH O), 6.99–7.04 m (1Н, Ph), 7.05–7.09 m (1H,
(6Н, CH ), 1.32 q (2Н, CH , J = 7.2), 1.61–1.72 m (2Н,
2
2
2
Ph), 7.20 d (1H, Ph, J = 8.0), 7.51 d (1H, Ph, J = 7.9),
CH ), 2.37 d (3Н, СН , J = 4.3), 2.86 t (2Н, CH , J = 7.7),
4.34 s (2Н, CH ), 5.23 s (1Н, OH), 5.46 s (2Н, CH O),
2 2
2 3 2
1
3
7
.99 s (1Н, CH ), 9.05 s (1Н, OH). С NMR spectrum
Py
(
5
1
DMSO-d ), δ , ppm: 14.31, 20.38, 20.84, 29.28, 39.54,
9.22, 110.76, 118.75, 121.36, 121.70, 128.94, 134.66,
7.03 t (1Н, Ph, J = 7.6), 7.07 t (1Н, Ph, J = 7.5), 7.23 d
(1H, Ph, J = 8.0), 7.51 d (1H, Ph, J = 7.8), 7.98 s (1Н,
6
C
13
35.65, 140.01, 142.73, 146.65, 150.03, 156.22. Mass
CH ), 9.00 s (1Н, OH). С NMR spectrum (DMSO-d ),
P
y
6
+
spectrum (MALDI-TOF), m/z: 312 [М + Н] . Found, %:
С 69.45; Н 6.66; N 13.81. С Н N O . Calculated, %:
С 69.42; Н 6.81; N 13.50.
δC, ppm: 14.42, 20.40, 22.56, 27.36, 27.49, 28.93, 29.30,
31.70, 39.49, 59.23, 110,77, 118.76, 121.37, 121.71,
128.93, 134.68, 135.75, 140.03, 142.74, 146.64, 149.97,
1
8
21
3
2
1
56.37. Mass spectrum (MALDI-TOF), m/z: 368 [М +
5
-(Hydroxymethyl)-2-methyl-4-{(2-pentyl-1H-
+
Н] . Found, %: С 71.45; Н 7.66; N 11.81. С Н N O .
Calculated, %: С 71.89; Н 7.97; N 11.44.
benzo[d]imidazol-1-yl)methyl}pyridine-3-ol (5c).
Yield 0.27 g (68%), mp 196–199°С. IR spectrum (KBr),
ν, cm : 1615 (С=N), 3194 (ОН). Н NMR spectrum
DMSO-d ), δ, ppm (J, Hz): 0.87 q (3Н, CH , J = 6.7),
22 29
3
2
–
1
1
5-(Hydroxymethyl)-2-methyl-4-{(2-undecyl-1H-
benzo[d]imidazol-1-yl)methyl}pyridine-3-ol (5f).
(
6
3
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 90 No. 9 2020