Sodium Azide → HCID 2725013, compound

Participants

Reaction Steps

Five grams (12.2 millimoles) of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide was dissolved in 120 ml of DMF, and 15.8 g (243 millimoles) of sodium azide was added with agitation. The reaction mixture was agitated at room temperature for a day and a night while shielded from light. The reaction mixture was added dropwise to 1,000 ml of ice water with agitation, and the insoluble material was extracted using 900 ml of methylene chloride. The organic phase was washed with ice water and dried using anhydrous sodium sulfate. The drying agent was separated by filtration, and the solvent was completely removed by distillation under reduced pressure. The pale yellow solid obtained was washed using diethyl ether, dried and recrystallized from 2-propanol to obtain 3.30 g (79% yield) of 2,3,4,6-tetra-O-acetyl-β-glucopyranosyl azide in the form of white needle shaped crystals. The physical properties of the product are shown below.

Provenance & Evidence