Reaction #985244

Reaction equation

sodium azide

p-toluenesulfonyl chloride

→

title compound

Yield 80.3%

p-toluenesulfonylazide

Yield 80.3%

Solvents

ethanol

H2O

ethanol

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise at 10-25° C.
2. 2
   Otherfollowed by reaction at room temperature for 2.5 hours
3. 3
   ConcentrationThe reaction solution was concentrated at room temperature under reduced pressure
4. 4
   WashThe resulting oily residue was washed with H2O several times
5. 5
   Dryingdried over anhydrous MgSO4
6. 6
   OtherAfter removing the drying agent
7. 7
   Filtrationby filtration

Procedure

After dissolving sodium azide (22.5 g, 0.35 mole) in a small amount of H2O, the resulting solution was diluted with a 90% ethanol aqueous solution (130 ml). To this, an ethanol solution dissolving p-toluenesulfonyl chloride (60 g, 0.32 mole) was added dropwise at 10-25° C., followed by reaction at room temperature for 2.5 hours. The reaction solution was concentrated at room temperature under reduced pressure. The resulting oily residue was washed with H2O several times and dried over anhydrous MgSO4. After removing the drying agent by filtration, there was obtained 50.7 g of the title compound as a colorless oil.

Source