Sodium Chloride → p-Toluenesulfonyl azide

HRID 456181Notes

Reaction equation

HRID 456181 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.[Cl-].[Na+]>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

6

Reactant 3

HCID 5234Sodium ChlorideHCID 73974-Toluenesulfonyl chlorideHCID 33557Sodium Azide

Product 1

HCID 13661p-Toluenesulfonyl azide

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 35 g. (0.5 moles) of sodium azide in 200 ml of water was placed in a 2 litre Erlenmeyer flask and diluted with 400 ml of 90% aqueous ethanol. To this solution was added with stirring a warm (45° C.) solution of 96 g. (0.50 mole) of p-toluenesulfonyl chloride in 1 litre of 99% ethanol. During the addition, sodium chloride separated. The reaction mixture was stirred at room temperature for 2.5 hours. Most of the solvent is removed at 35° C. (15 mm) with a rotary evaporator. The residue was mixed with 1.2 liters of water in a separatory funnel, and the oily p-toluenesulfonyl azide separated. This oil was washed with two 100 ml portions of water and dried over anhydrous sodium sulfate. Filtration with suction gave 50 g (60%, based on p-toluenesulfonyl chloride) of pure, colorless p-toluenesulfonyl azide which completely crystallised on standing at 5°.

Workup

  1. additionTo this solution was added
  2. customseparated
  3. stirringThe reaction mixture was stirred at room temperature for 2.5 hours
  4. customMost of the solvent is removed at 35° C. (15 mm)
  5. customwith a rotary evaporator
  6. additionThe residue was mixed with 1.2 liters of water in a separatory funnel
  7. customthe oily p-toluenesulfonyl azide separated
  8. washThis oil was washed with two 100 ml portions of water
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationFiltration with suction

Sources & evidence

ORD record
ord-018f69c692ce4506a3166fd8815aa013
Source dataset
uspto-grants-2013_07
Patent number
US08497384B2

Reaction notes

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