4-Toluenesulfonyl chloride → p-Toluenesulfonyl azide

HRID 1177938Notes

Reaction equation

HRID 1177938 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1>CC(C)=O.O>[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:1]=[N+:2]=[N-:3])(=[O:14])=[O:13])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 33557Sodium Azide

Product 1

HCID 13661p-Toluenesulfonyl azideYield 88.2%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

Sodium azide (2.7 g, 42 mmol) was added to a cold (0-4° C.) stirred solution of (4-methyl-benzenesulfonyl chloride (8 g, 42 mmol) in acetone:water (1:1, 240 mL) and continued stirring at 0° C. for 2 hr. Concentrated the reaction mixture to get the residue. The residue was extracted with diethyl ether and the organic phase was dried Na2SO4 and concentrated under reduced pressure to afford 7.3 g (88.2% yield) of 4-methyl-benzenesulfonyl azide.

Workup

  1. concentrationConcentrated the reaction mixture
  2. customto get the residue
  3. extractionThe residue was extracted with diethyl ether
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e7f4faa3c89349ce8008c460d6bfd202
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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