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

Participants

Reaction Steps

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.

Provenance & Evidence