making of diazotransfer reagents

ex. 2,4,6-triisopropylbenzenesulfonyl azide

1. reaction can be monitored by TLC. the azide is slightly less polar than the sulfonylchloride.

2. detailed reaction:
1. dissolve the tipscl in acetone.
2. add NaN3 into the reaction mixture. vigrous stirring for at least 20 min. NaN3 can't dissolve, a cloudy solution.
3. add water dropwise into the solution, until clear.
4. 1 hr, st gone.
5. wash with water, extracted into ether. dried, concentrated. sticky oil.
6. can be recrystallized in hexanes.

Note: if water was added at the very beginning, reaction can't go because tipscl can't dissolve in water.