4-Toluenesulfonyl chloride → p-Toluenesulfonyl azide

HRID 1038038Notes

Reaction equation

HRID 1038038 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[N-:12]=[N+:13]=[N-:14].[Na+]>CC(C)=O>[S:1]([N:12]=[N+:13]=[N-:14])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 33557Sodium Azide

Product 1

HCID 13661p-Toluenesulfonyl azideYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of tosyl chloride (4 g, 21 mmols) in acetone (60 ml) was added at 0-5 C a solution of sodium azide (1.37 g, 21 mmols) and the resulting solution was stirred at that temperature for 2 hours. Acetone was removed and the aqueous mixture was extracted with ether three times. The combined extracts were dried over MgSO4. Evaporation of solvents provided tosyl azide (4 g, 97%). (Eur. J. Org. Chem. 2003, 821-832.)

Workup

  1. customAcetone was removed
  2. extractionthe aqueous mixture was extracted with ether three times
  3. dry with materialThe combined extracts were dried over MgSO4
  4. customEvaporation of solvents

Sources & evidence

ORD record
ord-601214e066e04de0bf94676afc7c6f07
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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