反应详情

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).

1. customThe precipitate was isolated by filtration
2. washthe solid on the funnel was washed with DMAC (2 × 4 ml)
3. washthe solid was then washed with EtOH (5 ml) and H2O (2 × 3 ml)
4. additionThe addition of an equal volume of H2O to the DMAC filtrate
5. customafforded more product which
6. customwas isolated by filtration
7. washwashed with H2O
8. customEvaporation of the EtOH-H2O
9. customalso afforded more product, which
10. customwas triturated with Et2O
11. customisolated by filtration
12. customA sample obtained in this manner
13. customwas recrystallized from MeOH
14. customto give the pure product in about 50% recovery