3-Chloro-2-methylaniline → N2-(3-chloro-2-methylphenyl)-N-(4-methoxybenzyl)glycinamide

反応式

[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)=[O:19]>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([NH:5][CH2:17][C:18]([NH:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)=[O:19])[CH:6]=[CH:7][CH:8]=1

参加物

実験手順

3.93 g of 3-chloro-2-methylaniline was dissolved in 10 mL of DMF, and 2.00 g of potassium carbonate was added thereto, followed by portionwise addition of 3.55 g of 2-bromo-N-(4-methoxybenzyl)acetamide over 1 hour. The mixture was stirred at room temperature overnight, and ice water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30 to 30:70) to obtain 2.89 g of N2-(3-chloro-2-methylphenyl)-N-(4-methoxybenzyl)glycinamide.