Réaction #171053

Équation de réaction

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

NaN3

→

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

Rendement 79.4%

Solvants

water

DMF

Conditions de réaction

Traitement

1. 1
   Extractionextracted with EtOAc
2. 2
   LavageThe combined extracts were washed with 1M HCl and water successively
3. 3
   Séchagedried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Autreevaporated
6. 6
   AutreThe residue was purified by chromatography (Hex/EtOAc=4:1 to 2:1)

Mode opératoire

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).

Source