4-Toluenesulfonyl chloride → p-Toluenesulfonyl azide

HRID 1956111Notes

Reaction equation

HRID 1956111 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 sodium azide (22.5 g, 0.35 mole) in a small amount of H2O, the resulting solution was diluted with 90% ethanol aqueous solution (130 ml). To this, a solution of p-toluenesulfonyl chloride (60 g, 0.32 mole) in ethanol (300 ml) 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 several times with H2O and dried over anhydrous MgSO4. After removing the drying agent by filtration, there was obtained 50.7 g of p-toluenesulfonylazide as colorless oil.

Workup

  1. customfollowed by reaction at room temperature for 2.5 hours
  2. concentrationThe reaction solution was concentrated at room temperature under reduced pressure
  3. washThe resulting oily residue was washed several times with H2O
  4. dry with materialdried over anhydrous MgSO4
  5. customAfter removing the drying agent
  6. filtrationby filtration

Sources & evidence

ORD record
ord-a34a28315d9a46fba5c63920067385e3
Source dataset
uspto-grants-1998_07
Patent number
US05780206

Reaction notes

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