4-Toluenesulfonyl chloride → p-Toluenesulfonyl azide

HRID 898062Notes

Reaction equation

HRID 898062 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 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.

Workup

  1. additionwas added dropwise at 10-25° C.
  2. customfollowed by reaction at room temperature for 2.5 hours
  3. concentrationThe reaction solution was concentrated at room temperature under reduced pressure
  4. washThe resulting oily residue was washed with H2O several times
  5. dry with materialdried over anhydrous MgSO4
  6. customAfter removing the drying agent
  7. filtrationby filtration

Sources & evidence

ORD record
ord-943b16cb7d5b46f6a0f07b568d191b7f
Source dataset
uspto-grants-2008_04
Patent number
USRE040211E1

Reaction notes

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