Reactions and Syntheses by unknow

Author:unknow
Language: eng
Format: epub
ISBN: 9783527688746
Publisher: John Wiley & Sons, Inc.
Published: 2015-02-09T00:00:00+00:00

3.3.1.4 * 4-(p-Chlorophenyl)-3,4-dihydro-5-methoxycarbonyl-6-methylpyrimidin-2(1H)-one [5]

A solution of methyl acetoacetate (2.32 g, 20.0 mmol), 4-chlorobenzaldehyde (2.81 g, 20.0 mmol), urea (1.80 g, 30.0 mmol), and FeCl3 · 6H2O (1.35 g, 5.00 mmol) in EtOH (40 ml) containing four drops of concentrated HCl is heated under reflux for 5 h.

After cooling, the reaction mixture is poured onto crushed ice (200 g) and the resulting mixture is stirred for 15 min. The precipitate formed is collected by filtration and washed first with cold H2O (2 × 50 ml) and then with a mixture of EtOH/H2O (1 : 1, 3 × 40 ml). The crude product is dried and recrystallized from EtOH; colorless crystals, 4.85 g (83%), mp 200–201 °C.

IR (KBr): (cm−1) = 3364, 3218, 3093, 2947, 1712, 1687, 1633, 1488.

1H NMR (500 MHz, [D6]DMSO): δ (ppm) = 9.26 (s, 1H, NH), 7.78 (s, 1H, NH), 7.39 (d, J = 8.4 Hz, 2H, Ar), 7.25 (d, J = 8.4 Hz, 2H, Ar), 5.14 (d, J = 3.5 Hz, 1H, 4-H), 3.53 (s, 3H, OCH3), 2.25 (s, 3H, CH3).

13C NMR (126 MHz, [D6]DMSO): δ (ppm) = 165.7 (CO2Me), 151.9 (NC(O)N), 149.0 (C-6), 143.6, 131.8, 128.4, 128.1 (6 × Ar–C), 98.6 (C-5), 53.2, 50.8 (C-4, OCH3), 17.8 (CH3).

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