Sodium Azide → 6-Methoxyindan-1-ylmethylazide

HRID 1762574Notes

Reaction equation

HRID 1762574 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12]OS(C)(=O)=O)=[CH:5][CH:4]=1.[N-:18]=[N+:19]=[N-:20].[Na+]>CS(C)=O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12][N:18]=[N+:19]=[N-:20])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 17883324Methanesulphonic acid (6-methoxyindan-1-ylmethyl) ester

Product 1

HCID 230442196-Methoxyindan-1-ylmethylazide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

12.8 g (50 mmol) of methanesulphonic acid (6-methoxyindan-1-ylmethyl) ester and 5.2 g (80 mmol) of sodium azide are dissolved in 130 ml of dimethyl sulphoxide and stirred at 80° for 1 hour. The reaction mixture is poured onto ice-water and extracted by shaking with diethyl ether. The organic phases are washed twice with saturated sodium chloride solution, dried over magnesium sulphate and concentrated to dryness by evaporation under reduced pressure. 9.7 g of crude, oily 6-methoxyindan-1-ylmethylazide are obtained as residue.

Workup

  1. additionThe reaction mixture is poured onto ice-water
  2. extractionextracted
  3. stirringby shaking with diethyl ether
  4. washThe organic phases are washed twice with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness by evaporation under reduced pressure

Sources & evidence

ORD record
ord-310a4b1ec8814041abd90ec554d25036
Source dataset
uspto-grants-1989_05
Patent number
US04833169

Reaction notes

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