4-Toluenesulfonyl chloride → p-Toluenesulfonyl azide

HRID 351485Notes

Reaction equation

HRID 351485 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]1([CH3:15])[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1>O.C(O)C>[C:5]1([CH3:15])[CH:10]=[CH:9][C:8]([S:11]([N:1]=[N+:2]=[N-:3])(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 33557Sodium Azide

Product 1

HCID 13661p-Toluenesulfonyl azideYield 80.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

After dissolving 22.5 g (0.35 mole) of sodium azide in a small amount of water, the resulting solution was diluted with 130 ml of 90% hydrous ethanol. An ethanol solution having 60 g (0.32 mole) of p-toluenesulfonyl chloride dissolved therein was added dropwise to the solution at 10 to 25° C. They were reacted at room temperature for 2.5 hours. An oil obtained by concentrating the reaction mixture under reduced pressure was washed with water several times and then, dried over anhydrous magnesium sulfate. The desiccant was then removed, whereby 50.7 g of p-toluenesulfonyl azide was obtained as a colorless oil.

Workup

  1. dissolutiondissolved
  2. additiontherein was added dropwise to the solution at 10 to 25° C
  3. customThey were reacted at room temperature for 2.5 hours
  4. customAn oil obtained
  5. concentrationby concentrating the reaction mixture under reduced pressure
  6. washwas washed with water several times
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe desiccant was then removed

Sources & evidence

ORD record
ord-03952e9f01b74aefb10f39f5e833e516
Source dataset
uspto-grants-2004_06
Patent number
US06743562B2

Reaction notes

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