Sodium Azide → 3-(Azidopropyl)triethoxysilane

HRID 1486428Notes

Reaction equation

HRID 1486428 reaction equation
Cl[CH2:2][CH2:3][CH2:4][Si:5]([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8].[N-:15]=[N+:16]=[N-:17].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(=O)CC>[N:15]([CH2:2][CH2:3][CH2:4][Si:5]([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8])=[N+:16]=[N-:17]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 78771(3-Chloropropyl)triethoxysilane

Product 1

HCID 185193903-(Azidopropyl)triethoxysilaneYield 80%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 3-chloropropyltriethoxysilane (2.31 g, 9.6 mmol) and tetrabutylamonium iodide (0.020 g, 0.05 mmol) in butanone (25 mL) was added sodium azide (3.120 g, 48 mmol) and the reaction mixture was heated under reflux for 50 h. Filtration over celite was followed by evaporation of the solvent under vacuum. The residue was dissolved in dichloromethane (150 mL) and then washed with water (2 times 20 mL). The organic phase was dried (NaSO4) and evaporated to give the desired product (1.9 g).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 50 h
  3. filtrationFiltration over celite
  4. customwas followed by evaporation of the solvent under vacuum
  5. dissolutionThe residue was dissolved in dichloromethane (150 mL)
  6. washwashed with water (2 times 20 mL)
  7. dry with materialThe organic phase was dried (NaSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-82403969c99d43b094318dd050c7f8db
Source dataset
uspto-grants-2016_08
Patent number
US09427406B2

Reaction notes

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