Sodium Azide → (3-Azidopropyl)(trimethoxy)silane

HRID 1578232Notes

Reaction equation

HRID 1578232 reaction equation
[CH3:1][O:2][Si:3]([O:10][CH3:11])([O:8][CH3:9])[CH2:4][CH2:5][CH2:6]Cl.[N-:12]=[N+:13]=[N-:14].[Na+].[N-]=[N+]=[N-]>CO>[CH3:1][O:2][Si:3]([O:10][CH3:11])([O:8][CH3:9])[CH2:4][CH2:5][CH2:6][N:12]=[N+:13]=[N-:14]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 33558AzideHCID 624493-(Trimethoxysilyl)propyl chloride2×

Product 1

HCID 20490145(3-Azidopropyl)(trimethoxy)silane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 2 liter, 3-necked round bottom glass flask fitted with a stirrer, heating mantle, reflux condenser, and nitrogen inlet source was charged 99 grams (0.5 mole) of a 3-trimethoxysilylpropylchloride, 112 grams (1.72 moles) sodium azide and 1 liter of methanol. The mixture was stirred at reflux temperature for 11 days, cooled to about 10 C. in a wet-ice bath and filtered. The filtrate was concentrated under vacuum on a steam bath. The semi-solid sludge was treated with 0.2 liter n-heptane, filtered and again concentrated under vacuum on a warm water bath. Continued distillation gave a 62 mole % yield of product (74 C./63 mm) comprised of 92 wt.% azide product and 8 wt.% 3-trimethoxysilylpropylchloride.

Workup

  1. customTo a 2 liter, 3-necked round bottom glass flask fitted with a stirrer
  2. temperatureheating mantle
  3. temperaturereflux condenser, and nitrogen inlet source
  4. temperatureat reflux temperature for 11 days
  5. temperaturecooled to about 10 C
  6. filtrationin a wet-ice bath and filtered
  7. concentrationThe filtrate was concentrated under vacuum on a steam bath
  8. additionThe semi-solid sludge was treated with 0.2 liter n-heptane
  9. filtrationfiltered
  10. concentrationagain concentrated under vacuum on a warm water bath
  11. distillationdistillation
  12. customgave a 62 mole % yield of product (74 C./63 mm)

Sources & evidence

ORD record
ord-aa1c86644f8847fd9dd3045a040370af
Source dataset
uspto-grants-1981_09
Patent number
US04292234

Reaction notes

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