4-Toluenesulfonyl chloride → p-Toluenesulfonyl azide

HRID 1350521Notes

Reaction equation

HRID 1350521 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[N-:12]=[N+:13]=[N-:14].[Na+]>C(O)C.O>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([N:12]=[N+:13]=[N-:14])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 33557Sodium Azide

Product 1

HCID 13661p-Toluenesulfonyl azideYield 94.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Dissolve 4-toluenesulphonyl chloride (481.3 g; 2.52 mol) in hot ethanol (2900 ml) and allow the resulting clear solution to cool to room temperature. Dissolve sodium azide (198.31 g; 3.05 mol) in water (360 ml) and mix the two solutions with stirring. Allow the mixture to stand for one and a half hours at room temperature, pour onto water (7250 ml) and separate the resulting two phase mixture, wash the clear oil with water, dry over magnesium sulphate and filter to leave the desired 4-toluene sulphonyl azide (weight=470.57 g).

Workup

  1. waitAllow the mixture to stand for one and a half hours at room temperature
  2. additionpour onto water (7250 ml)
  3. customseparate the resulting two phase mixture
  4. washwash the clear oil with water
  5. dry with materialdry over magnesium sulphate
  6. filtrationfilter

Sources & evidence

ORD record
ord-e7cc6d6f01f24cdab5c00ac8be613680
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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