反応 #171053

反応方程式

4-(4-bromo-2-methyl-3-oxobutan-2-yl)-2-chlorobenzenesulfonamide

NaN3

→

4-(4-azido-2-methyl-3-oxobutan-2-yl)-2-chlorobenzenesulfonamide

収率 79.4%

溶媒

water

DMF

反応条件

後処理

1. 1
   抽出extracted with EtOAc
2. 2
   洗浄The combined extracts were washed with 1M HCl and water successively
3. 3
   乾燥dried over MgSO4
4. 4
   ろ過filtered
5. 5
   その他evaporated
6. 6
   その他The residue was purified by chromatography (Hex/EtOAc=4:1 to 2:1)

実験手順

To a solution of 4-(4-bromo-2-methyl-3-oxobutan-2-yl)-2-chlorobenzenesulfonamide (11.3 g, 31.8 mmol) in DMF (50 mL) was added NaN3 (3.1 g, 47.8 mmol, 1.5 eq) at 0° C. After stirring 2 h, the residue was diluted with water and extracted with EtOAc. The combined extracts were washed with 1M HCl and water successively, dried over MgSO4, filtered and evaporated. The residue was purified by chromatography (Hex/EtOAc=4:1 to 2:1) to give 4-(4-azido-2-methyl-3-oxobutan-2-yl)-2-chlorobenzenesulfonamide (8.0 g, 79% yield) as yellow sticky oil. 1H NMR (400 MHz, CDCl3) δ 8.11 (d, J=8.4 Hz, 1H), 7.43 (s, 1H), 7.29 (d, J=2.2 Hz, 1H), 5.12 (s, 2H), 4.11 (s, 2H), 1.58 (s, 6H).

出典