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

HRID 2194824

반응식

HRID 2194824 반응식
[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

참가 물질

5

반응물 2

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

생성물 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 ester수율 170.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-1e9d1a8365ba4549bb5a6643109fe6c8
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334313B2

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