Methyl 3-isocyanatobenzoate → 3-[3-(2,2-Diethoxyethyl)-3-(4-isopropylphenyl)ureido]benzoic acid methyl ester

HRID 600926

Reaktionsgleichung

Reaktionsgleichung von HRID 600926
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH:12]([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:19]([C:23]1[CH:24]=[C:25]([N:29]=[C:30]=[O:31])[CH:26]=[CH:27][CH:28]=1)([O:21][CH3:22])=[O:20]>ClCCl>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:11]=[CH:12][N:29]([C:25]3[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=3)[C:19]([OH:21])=[O:20])[C:30]2=[O:31])=[CH:8][CH:9]=1)([CH3:2])[CH3:3].[CH3:22][O:21][C:19](=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:30]([N:10]([CH2:11][CH:12]([O:13][CH2:14][CH3:15])[O:16][CH2:17][CH3:18])[C:7]2[CH:8]=[CH:9][C:4]([CH:1]([CH3:2])[CH3:3])=[CH:5][CH:6]=2)=[O:31])[CH:24]=1

Komponenten

5

Edukt 2

HCID 2733366Methyl 3-isocyanatobenzoateHCID 196009444-Isopropyl-N-(2,2-diethoxyethyl)aniline

Produkt 2

HCID 103140423-[3-(4-Isopropylphenyl)-2-oxo-2,3-dihydroimidazol-1-yl]benzoic acidHCID 666034673-[3-(2,2-Diethoxyethyl)-3-(4-isopropylphenyl)ureido]benzoic acid methyl esterAusbeute 170,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of N-(4-isopropylphenyl)-2,2-diethoxyethylamine (0.50 g, 2.0 mmol) prepared above and 3-carbomethoxyphenyl isocyanate (0.36 g, 2.05 mmol) in dry dichloromethane (10 mL) was stirred at room temperature overnight. The solution was then chromatographed (silica gel, hexanes:ethyl acetate, 8:2) to give the pure urea, 3-[3-(2,2-diethoxyethyl)-3-(4-isopropylphenyl)ureido]benzoic acid methyl ester as a colorless oil (0.73 g, 85.3%). MS (ES−) m/z: 427. This was then stirred with HCl (0.5 M, 50 mL) at 80° C. for 4 h. After cooling to room temperature, the white precipitate formed was collected and purified by chromatography (silica gel, dichloromethane:ethyl acetate, 9:1) to give pure methyl 3-[3-(4-isopropylphenyl)-2-oxo-2,3-dihydroimidazol-1-yl]benzoate as white solid [0.42 g, 73.7%, MS (ES+) m/z: 337]. The solid was then treated with boron tribromide in dichloromethane (1.0 M, 4.0 mL) at room temperature overnight. The volatiles were removed in vacuum and the residue was suspended in water and stirred for 30 min. The solid was collected by filtration and washed with water to furnish 3-[3-(4-isopropylphenyl)-2-oxo-2,3-dihydroimidazol-1-yl]benzoic acid (0.40 g, 100%). m.p. 283-285° C. 1H NMR (CDCl3, 300 MHz) δ (ppm) 1.24 (d, 6H), 2.84-3.00 (m, 1H), 6.69 (d, 1H), 6.74 (d, 1H), 7.26 (d, 2H), 7.45-7.54 (m, 3H), 7.91 (d, 1H), 8.02 (d, 1H), 8.12 (s, 1H). MS (ES−) m/z: 321.

Aufarbeitung

  1. customThe solution was then chromatographed (silica gel, hexanes:ethyl acetate, 8:2)

Quellen und Nachweise

ORD-Eintrag
ord-1a415a6870b04f00b8828f7e50c4512e
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902241B2

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