Sodium Iodide → HCID 86659031, compound

HRID 1776447Notes

Reaction equation

HRID 1776447 reaction equation
Br[CH2:2][CH2:3][C:4]([C@@H:6]([C@H:8]([C@@H:10]([C@@H:12]([CH2:14][OH:15])[OH:13])[OH:11])[OH:9])[OH:7])=[O:5].[N-:16]=[N+:17]=[N-:18].[Na+].[I-].[Na+]>O>[N:16]([CH2:2][CH2:3][C:4]([C@@H:6]([C@H:8]([C@@H:10]([C@@H:12]([CH2:14][OH:15])[OH:13])[OH:11])[OH:9])[OH:7])=[O:5])=[N+:17]=[N-:18]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 86659032HCID 86659032, compound

Product 1

HCID 86659031HCID 86659031, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 5 L round bottom three-necked flask, equipped with a heating mantle, an overhead stirrer, and a thermometer, was charged with 150 gm bromoethylglucose (525 mmol). The oil was dissolved in 2 L water and treated with 68.3 gm sodium azide (1.05 mol, 2 equiv.; 65 gm/mol; Alfa-Aesar) followed by 7.9 gm sodium iodide (52.5 mmol, 0.08 equiv.; 149.89 gm/mol; Alfa-Aesar) and the solution warmed to 50 C and stirred overnight. The solution was cooled to room temperature and concentrated to dryness on the rotovap. The solid residue was digested with 3×500 mL of 5:1 vol. CHCl3:MeOH at 40 C. The combined organic portions were filtered and evaporated to dryness to afford azidoethylglucose (86 gm) as an off-white solid. TLC (20% MeOH/DCM; char with H2SO4): single spot, indistinguishable from the starting material.

Workup

  1. customA 5 L round bottom three-necked flask, equipped with a heating mantle, an overhead stirrer
  2. temperaturethe solution warmed to 50 C
  3. concentrationconcentrated to dryness on the rotovap
  4. filtrationThe combined organic portions were filtered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-394cbae492e34bd4946ca7dc39d529d4
Source dataset
uspto-grants-2016_02
Patent number
US09265838B2

Reaction notes

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