Sodium hydride → 1-[6-(4-Bromophenoxy)hexyl]-3-(4-methyl-1,3-thiazol-2-yl)-2-imidazolidinone

反応式

[CH3:1][C:2]1[N:3]=[C:4]([N:7]2[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[S:5][CH:6]=1.[H-].[Na+].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br)=[CH:18][CH:17]=1>CN(C)C=O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:9]2[CH2:10][CH2:11][N:7]([C:4]3[S:5][CH:6]=[C:2]([CH3:1])[N:3]=3)[C:8]2=[O:12])=[CH:18][CH:17]=1

参加物

実験手順

To a suspension of 1-(4-methyl-1,3-thiazol-2-yl)-2-imidazolidinone (0.11 g, 0.61 mmol) dissolved in 10 mL of dimethylformamide at 0° C. was added NaH (60% dispersion in mineral oil, 36.6 mg, 0.92 mmol). The mixture was stirred at room temperature for 30 minutes and then cooled in ice bath. 1-Bromo-4-[(6-bromohexyl)oxy] benzene (0.21 g, 0.61 mmol) was added, and the mixture was stirred at room temperature for additional 4 hours. The reaction was quenched with methanol, and the solvents were removed under reduced pressure. A saturated aqueous NH4Cl solution and dichloromethane were successively added to the residue. The dichloromethane layer was separated and dried over MgSO4, filtered, evaporated, and purified by column chromatography (ethyl acetate:MeOH=10:1) to give the product (i.e., Compound 10) as a yellow viscous oil (0.19 g, 74%).