4-Toluenesulfonyl chloride → p-Toluenesulfonyl azide

HRID 1655491Notes

Reaction equation

HRID 1655491 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 azide

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Sodium azide (22.5 g, 0.35 mol) was dissolved in H2O(65 ml) and diluted with 90% aqueous ethanol (130 ml). To this mixture, a solution of p-toluenesulfonyl chloride (60 g, 0.32 mol) in ethanol (300 ml) was added dropwise at 10°-25° C. and stirring was continued for 2.5 hours at room temperature. The reaction mixture was evaporated under reduced pressure, the resultant residue was washed with H2O for several times, dried over anhydrous MgSO4 and filtered with suction to give the title compound as a colorless oil; yield: 50.7 g.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. washthe resultant residue was washed with H2O for several times
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered with suction

Sources & evidence

ORD record
ord-729cf832a1ec4c7987e9c52bff1a7c6e
Source dataset
uspto-grants-1993_10
Patent number
US05250669

Reaction notes

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