Реакция #463556

Уравнение реакции

1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamine

3-nitrophthalic anhydride

→

2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-nitroisoindoline-1,3-dione

Выход 81.0%

Растворители

acetic acid

Условия реакции

Обработка

1. 1
   Температураat reflux for 15 h
2. 2
   ДругоеThe solvent was removed in vacuo
3. 3
   Другоеto yield an oil

Методика

A stirred solution 1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamine (640 mg, 2.34 mmol) and 3-nitrophthalic anhydride (460 mg, 2.34 mmol) in acetic acid (10 mL) was heated at reflux for 15 h. The solvent was removed in vacuo to yield an oil. Chromatography of the resulting oil yielded 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-nitroisoindoline-1,3-dione as a yellow solid (850 mg, 81% yield): mp, 110.0-114.0° C.; 1H NMR (CDCl3); δ 1.47 (t, J=7.0 Hz, 3H, CH3), 2.90 (s, 3H, CH3), 3.71 (dd, J=4.3, 14.4 Hz, 1H, CHH), 3.85 (s, 3H, CH3), 4.10 (q, J=7.0 Hz, 2H, CH2), 4.58 (dd, J=10.7, 14.4 Hz, 1H, CHH), 5.93 (dd, J=4.2, 10.7 Hz, 1H, NCH), 6.84 (d, J=8.8 Hz, 1H, Ar), 7.11-7.15 (m, 2H, Ar), 7.89 (t, J=7.8 Hz, 1H, Ar), 8.08-8.13 (m, 2H, Ar); 13C NMR (CDCl3) δ 14.67, 41.56, 49.19, 53.97, 55.96, 64.56, 111.52, 112.51, 120.62, 123.44, 127.35, 128.65, 128.84, 133.73, 135.48, 145.24, 148.68, 149.92, 162.53, 165.33; Anal Calcd for C20H20NO8S: C, 53.57; H, 4.50; N, 6.23. Found: C, 53.54; H, 4.28; N, 6.32

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