Methanol → p-Toluenesulfonyl azide

HRID 1417134Notes

Reaction equation

HRID 1417134 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CO.[S:7](Cl)([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)(=[O:9])=[O:8]>O>[S:7]([N:1]=[N+:2]=[N-:3])([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 73974-Toluenesulfonyl chloride2×HCID 33557Sodium Azide3×

Product 1

HCID 13661p-Toluenesulfonyl azide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In a 250 ml round bottom flask was added 60 ml of deionized (DI) water and 21 g (0.32 mole) of sodium azide. It was mixed at room temperature for 15 minutes until all the sodium azide was in solution. In a 1 liter round bottom flask was added 300 ml of methanol and 50.1 g (0.26 moles) of toluenesulfonyl chloride(tosyl chloride). The solution was mixed at room temperature until all of the tosyl chloride was dissolved. The sodium azide solution was added to the tosyl chloride solution and mixed for 1 hour. The solution darkened and a second phase formed. After the 1 hour hold the reaction was poured into 1200 ml of 20° C. DI water. Two phases formed and the bottom layer was kept. The bottom layer was washed twice with 100 ml of DI water. The yield was 32.4 grams.

Workup

  1. dissolutionwas dissolved
  2. additionmixed for 1 hour
  3. customa second phase formed
  4. customAfter the 1 hour
  5. additionwas poured into 1200 ml of 20° C
  6. customTwo phases formed
  7. washThe bottom layer was washed twice with 100 ml of DI water

Sources & evidence

ORD record
ord-d65b7a8da76a42508474aff95cabb94f
Source dataset
uspto-grants-1999_03
Patent number
US05876897

Reaction notes

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