Реакция #725877

Уравнение реакции

N-toluenesulfonyl-2-(3,5-di(trifluoroacetylamino)benzoyl)pyrrole

KOH

→

2-(3,5-diaminobenzoyl)pyrrole

Выход 65.0%

Растворители

EtOH

Условия реакции

Обработка

1. 1
   Температураthe mixture was heated
2. 2
   Температураat reflux until TLC analysis
3. 3
   ДругоеThe crude product was purified by column chromatography (SiO2, CH2Cl2:MeOH)

Методика

To a stirred EtOH (10 mL) solution of N-toluenesulfonyl-2-(3,5-di(trifluoroacetylamino)benzoyl)pyrrole (1.00 g, 1.83 mmol), was added 40% KOH solution (2 mL) and the mixture was heated at reflux until TLC analysis showed complete conversion. The resulting solution was cooled to room temperature and worked up as in Example 7. The crude product was purified by column chromatography (SiO2, CH2Cl2:MeOH) to afford the purified product 2-(3,5-diaminobenzoyl)pyrrole (237 mg, 65% yield). 1H NMR (500 MHz, CD3OD, 25° C.) δ 2.43 (s, 3H), 6.45 (m, 1H), 6.90 (m, 1H), 7.41 (d, 2H), 7.88 (m, 3H), 7.93 (d, 2H), 8.39 (t, 1H); 13C NMR (100 MHz, CD3OD, 25° C.) δ 104.8, 105.7, 109.4, 119.5, 125.2, 130.5, 139.8, 147.8, 186.0; HRMS (EI): m/z 201.0896 (100) {M}+.

Источник