Réaction #725877

Équation de réaction

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

KOH

→

2-(3,5-diaminobenzoyl)pyrrole

Rendement 65.0%

Solvants

EtOH

Conditions de réaction

Traitement

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

Mode opératoire

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}+.

Source