N-[2-(4-氨基苯基)乙基]乙酰胺

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of N-[2-(4-aminophenyl)ethyl]acetamide (713 mg, 4 mmoles) and I (672 mg, 2 mmoles) in DMAC (8 ml) was stirred under N2 at about 25° in a stoppered flask protected from light for 2 days. The precipitate was isolated by filtration and the solid on the funnel was washed with DMAC (2 × 4 ml). The filtrate was set aside, and the solid was then washed with EtOH (5 ml) and H2O (2 × 3 ml). The addition of an equal volume of H2O to the DMAC filtrate afforded more product which was isolated by filtration and washed with H2O. Evaporation of the EtOH-H2O washes also afforded more product, which was triturated with Et2O and isolated by filtration. The combined yield was 70% (609 mg). A sample obtained in this manner was recrystallized from MeOH to give the pure product in about 50% recovery. Anal. Calcd for C17H20N8O.HBr.2H2O: C, 43.50; H, 5.37; N, 23.88. Found: C, 43 .40; H, 5.42; N, 23.82. Spectral data: λ max, nm (ε × 10-3), 0.1 N HCl, 246 (17.9), 292 (5.80), 337 (10.2), 347 (sh); pH 7, 257 (27.6), 280 (sh), 372 (7.70); 0.1 N NaOH, 257 (28.6), 280 (sh), 372 (7.96); pmr (DMSO-d6), δ 1.76 (s, 3, CH3), 2.56 (m, 2, C6H4 --CH 2 CH2), 3.16 (m, 2, CH2NHCO), 4.52 (s, 2, CH2NHC6H4), 6.80 (m, 4, C6H4), 8.84 (s, 1, C7 --H). The precipitate was isolated by filtration the solid on the funnel was washed with DMAC (2 × 4 ml) the solid was then washed with EtOH (5 ml) and H2O (2 × 3 ml) The addition of an equal volume of H2O to the DMAC filtrate afforded more product which was isolated by filtration washed with H2O Evaporation of the EtOH-H2O also afforded more product, which was triturated with Et2O isolated by filtration A sample obtained in this manner was recrystallized from MeOH to give the pure product in about 50% recovery