反応 #72485

反応方程式

4-aminophenol

4-chloro-N-(3-chloro-quinoxalin-2-yl)-benzenesulfonamide

→

compound 5-4

収率 60.0%

4-Chloro-N-[3-(4-hydroxy-phenylamino)-quinoxalin-2-yl]-benzenesulfonamide

収率 60.0%

溶媒

反応条件

後処理

1. 1
   温度The reaction mixture was heated
2. 2
   温度under reflux in an inert atmosphere of nitrogen for 25 h
3. 3
   その他Reaction progress
4. 4
   その他Upon completion of the reaction
5. 5
   温度the mixture was cooled

実験手順

A solution of 4-aminophenol (22 mg, 0.2 mmol) in xylenes (2 mL), was treated with 4-chloro-N-(3-chloro-quinoxalin-2-yl)-benzenesulfonamide (35.4 mg, 0.1 mmol) in one portion. The reaction mixture was heated under reflux in an inert atmosphere of nitrogen for 25 h. Reaction progress was monitored by TLC. Upon completion of the reaction, the mixture was cooled, which resulted in compound 5-4 precipitating from the solution as red-yellow crystals. The crystals were filtered and washed with hot methanol (5 mL) and pentane (5×5 mL). Yield 60%, mp=298-301° C. TLC Rf=0.35 (hexanes/EtOAc 1:1). 1H NMR (DMSO-d6, 600 MHz): δ 6.75 (d, J=8.4 Hz, 2H), 7.30 (t, J=7.2 Hz, 1H), 7.35 (t, J=7.2 Hz, 1H), 7.66 (d, J=8.4 Hz, 2H), 7.69 (d, J=7.8 Hz, 2H), 7.89 (br.s, 1H), 8.11 (d, J=7.8 Hz, 2H), 8.81 (br.s, 1H), 9.30 (br.s, 1H), 12.29 (br.s, 1H). HPLC/MS: [M+H]+ m/z 426. HRMS: Calcd. [M+H]+ m/z 427.0632, Observed 427.0644.

出典