4-Toluenesulfonyl chloride → p-Toluenesulfonyl azide

HRID 2259821Notes

Reaction equation

HRID 2259821 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>[S:11]([N:1]=[N+:2]=[N-:3])([C:8]1[CH:9]=[CH:10][C:5]([CH3:15])=[CH:6][CH:7]=1)(=[O:13])=[O:12]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 33557Sodium Azide

Product 1

HCID 13661p-Toluenesulfonyl azideYield 77.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 3776IsopropanolSolvent

Procedure

Tosyl azide was prepared as follows. A solution of sodium azide (58.5 g, 0.90 tool) in distilled water (170 mL) was quickly added to a stirred suspension (partly in solution) of p-toluenesulfonyl chloride (143.0 g, 0.75 tool) in isopropanol (850 mL) contained in a beaker at room temperature. The mixture was stirred for one hour, then poured into 3 L of distilled water and stirred for one more hour. The separated oily tosyl azide was washed three times with water, dried over anhydrous magnesium sulfate, then dried by stirring under vacuum. It is important for its use as a reagent in the lithiation reaction that tosyl azide is substantially pure (free of impurities) and contains a negligible amount of water (measured by proton NMR). 114 g of colourless tosyl azide oil was obtained (yield 77%). A 95% yield could be obtained by extracting the drying agent with chloroform. 1HNMR: δ=7.84 H-ortho-sulfonyl (2H d, J≈8.3); δ=7.41 H-orthomethyl (2H d, J≈8.3); δ=2.49 Me (3H s).

Workup

  1. customTosyl azide was prepared
  2. customcontained in a beaker at room temperature
  3. stirringstirred for one more hour
  4. washThe separated oily tosyl azide was washed three times with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customdried
  7. stirringby stirring under vacuum
  8. customIt is important for its use as a reagent in the lithiation reaction that tosyl azide

Sources & evidence

ORD record
ord-7dbd8bd11ca342e19aafa318cbc330d7
Source dataset
uspto-grants-1995_12
Patent number
US05475065

Reaction notes

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