SYNTHESIS OF p-AMINOBENZOIC ACID DIAMIDES
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6.83–6.89 m (2Н, С6Н4О), 7.28 br.d (1Н, Н4, С6Н4СF3,
J 7.7), 7.31–7.37 m (2Н, С6Н4О), 7.45 br.t (1Н, Н5,
С6Н4СF3, J 8.0), 7.71–7.76 m and 7.88–7.93 m (4Н,
С6Н4N), 8.08 br.d (1Н, Н6, С6Н4СF3, J 8.2), 8.19 br.t
(1Н, Н2, С6Н4СF3, J 1.9), 9.17 br.s (1Н, NНС6Н4),
9.04 br.s (1Н, NНС6Н4СF3). Found, %: С 65.31; Н
4.93; N 5.49. С27Н25F3N2О4. Calculated, %: С 65.05;
Н 5.05; N 5.62.
(IXb). Yield 75%, mp 202–204°C, Rf 0.50. H NMR
spectrum, δ, ppm (J, Hz): 1.83–1.95 m and 2.00–2.10
m (4H, СН2С), 3.40 d (2Н, NСН2, J 6.1), 3.42–3.47 m
and 3.68–3.76 m (4Н, СН2О), 3.79 s and 3.87 s (6Н,
ОСН3), 6.82 m and 6.97 m (4Н, С6Н4О), 7.27 m and
7.68 m (4Н, С6Н4СО), 7.47 br.t (1Н, NНСН2, J 6.1),
7.83 m and 7.98 m (4Н, С6Н4N), 10.02 s (1Н, NН).
Found, %: С 70.67; Н 6.52; N 6.02. С28Н30N2О5.
Calculated, %: С 70.87; Н 6.37; N 5.90.
4-(4-Methoxyphenyl)-N-[4-(2-methoxy-5-methyl-
phenylcarbamoyl)phenyl]tetrahydro-2H-pyran-4-
carboxamide (VIIh). Yield 73%, mp 210–212°C
4-Bromo-N-{4-[4-(4-methoxyphenyl)tetrahydro-
2H-pyran-4-ylmethylcarbamoyl]phenyl}benzamide
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(ethanol), Rf 0.49. H NMR spectrum, δ, ppm: 1.91–
(IXc). Yield 72%, mp 208–210°C, Rf 0.54. H NMR
2.03 m (2Н, СН2), 2.33 s (3Н, СН3), 2.54–2.63 m (2Н,
СН2), 3.53–3.63 m and 3.74–3.82 m (4Н, ОСН2), 3.77
s (3Н, ОСН3), 3.89 s (3Н, СН3ОС6Н3), 6.81–6.83 m
(2Н, Н3,4, С6Н3), 6.83–6.88 m and 7.30–7.36 m (4Н,
С6Н4О), 7.73–7.81 m (4Н, С6Н4N), 8.03 br.s (1Н, Н6,
С6Н3), 8.65 br.s (1Н, NНС6Н3), 9.16 br.s (1Н, NН).
Found, %: С 70.59; Н 6.51; N 5.79. С28Н30N2О5. Cal-
culated, %: С 70.87; Н 6.37; N 5.90.
spectrum, δ, ppm (J, Hz): 1.85–1.95 m and 1.98–2.05
m (4H, СН2С), 3.39 d (2Н, NСН2, J 6.1), 3.42–3.48 m
and 3.68–3.76 m (4Н, СН2О), 3.79 s (3Н, ОСН3), 6.83
m and 7.23 m (4Н, С6Н4О), 7.48 br.t (1Н, NНСН2, J
6.1), 7.63 m and 7.83 m (4Н, С6Н4Br), 7.79 m and
7.98 m (4Н, С6Н4N), 10.12 s (1Н, NН). Found, %: С
61.73; Н 5.32; N 5.51. С27Н27 BrN2О4. Calculated, %:
С 61.96; Н 5.20; N 5.35.
Amic acids VIIIa–VIIIf were obtained according
to procedure described in Refs. [7, 8].
N-[4-(4-Methoxyphenyl)tetrahydro-2H-pyran-4-
ylmethyl]-4-(2-phenoxyacetylamino)benzamide (IXd).
Yield 75%, mp 172–174°C, Rf 0.56. 1H NMR spectrum,
δ, ppm (J, Hz): 1.85–1.95 m and 1.98–2.07 m (4H,
СН2С), 3.39 d (2Н, NСН2, J 6.1), 3.42–3.48 m and
3.70–3.77 m (4Н, СН2ОСН2), 3.79 s (3Н, ОСН3), 4.61
s (2Н, ОСН2), 6.82–6.91 m and 6.95–7.00 m (5Н,
С6Н5), 7.24–7.32 m (4Н, С6Н4О), 7.53 br.t (1Н, NНСН2,
J 6.1), 7.69 s (4Н, С6Н4), 9.98 s (1Н, NН). Found, %:
С 70.66; Н 6.52; N 5.77. С28Н30N2О5. Calculated, %:
С 70.87; Н 6.37; N 5.90.
Diamides IXa–IXf. A mixture of 0.01 mol of acid
VIII and 0.015 mol of thionyl chloride in anhydrous
toluene was refluxed during 8–10 h. After the solvent
removal, the residue was dissolved in 30 mL of
anhydrous dioxane. The obtained mixture was added
dropwise at 15–18°C to a solution of 0.01 mol of [4-
(4-methoxyphenyl)tetrahydro-2H-pyran-4-yl]methyl-
amine III and 0.01 mol of triethylamine in 50 mL of
anhydrous dioxane. The reaction mixture was refluxed
during 5 h, cooled, and poured into 100–150 mL of
water. The formed crystals were filtered off, washed
sequentially with dilute hydrochloric acid (1 : 3),
water, 5% sodium hydroxide solution, and water, dried,
and recrystallized from ethanol.
4-(2,2-Diphenylacetylamino)-N-[4-(4-methoxyphenyl)-
tetrahydro-2H-pyran-4-ylmethyl]benzamide (IXe).
Yield 76%, mp 165–167°C, Rf 0.59. 1H NMR spectrum,
δ, ppm (J, Hz): 1.84–1.94 m and 1.97–2.06 m (4Н,
СН2С), 3.38 d (2Н, NСН2, J 6.1), 3.40–3.46 m and
3.68–3.76 m (4Н, СН2ОСН2), 3.78 s (3Н, ОСН3), 5.14
s (1Н, СНPh2), 6.82–6.87 m (2Н, С6Н4О), 7.17–7.31
m and 7.34–7.38 m (12Н, Ph, С6Н4О), 7.46 br.t (1Н,
NНСН2, J 6.1), 7.65 s (4Н, С6Н4N), 10.30 s (1Н, NН).
Found, %: С 76.68; Н 6.29; N 5.15. С34Н34N2О4.
Calculated, %: С 76.38; Н 6.41; N 5.24.
N-{4-[4-(4-Methoxyphenyl)tetrahydro-2H-pyran-
4-ylmethylcarbamoyl]phenyl}benzamide (IXa). Yield
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79%, mp 195–197°C, Rf 0.53. H NMR spectrum, δ,
ppm (J, Hz): 1.81–1.92 m and 1.99–2.08 m (4H,
СН2С), 3.39 d (2Н, NСН2, J 6.1), 3.41–3.46 m and
3.68–3.76 m (4Н, СН2О), 3.79 s (3Н, ОСН3), 6.83 m
and 7.23 m (4Н, С6Н4О), 7.43 m (3Н, С6Н5), 7.46 br.t
(1Н, NНСН2, J 6.1), 7.68 m (2Н, С6Н5), 7.81 m and
7.98 m (4Н, С6Н4N), 10.19 s (1Н, NН). Found, %: С
72.67; Н 6.51; N 6.18. С27Н28N2О4. Calculated, %: С
72.95; Н 6.35; N 6.30.
N-{4-[4-(4-Methoxyphenyl)tetrahydro-2H-pyran-
4-ylmethylcarbamoyl]phenyl}furan-2-carboxamide
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(IXf). Yield 69%, mp 153–155°C, Rf 0.55. H NMR
spectrum, δ, ppm (J, Hz): 1.82–1.92 m and 1.99–2.08
m (4H, СН2С), 3.39 d (2Н, NСН2, J 6.1), 3.41–3.47 m
and 3.68–3.75 m (4Н, СН2О), 3.79 s (3Н, ОСН3), 6.59
d.d (1Н, Н4, furan, J 3.5, 1.7), 6.86 m and 7.25 m (5Н,
4-Methoxy-N-{4-[4-(4-methoxyphenyl)tetrahydro-
2H-pyran-4-ylmethylcarbamoyl]phenyl}benzamide
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 5 2015