Sodium Azide → 6-Azidohexan-1-ol

HRID 2172168Notes

Reaction equation

HRID 2172168 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[N-:9]=[N+:10]=[N-:11].[Na+]>CN(C=O)C>[N:9]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8])=[N+:10]=[N-:11]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 779706-Bromo-1-hexanol

Product 1

HCID 110517786-Azidohexan-1-olYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

6-Bromo-1-hexanol (5.00 g, 27.6 mmol) was dissolved in 12 mL of DMF. To this solution, sodium azide (4.00 g, 61.5 mmol) was added and the mixture was stirred at 50° C. for 3 days. The mixture was concentrated by evaporation, and distilled water (10 mL) was added thereto. This aqueous solution was extracted six times with diethyl ether, and the combined organic extracts were dried over magnesium sulfate, followed by evaporation to give a product (6-azido-1-hexanol). The yield was 99% or more.

Workup

  1. concentrationThe mixture was concentrated by evaporation
  2. distillationdistilled water (10 mL)
  3. additionwas added
  4. extractionThis aqueous solution was extracted six times with diethyl ether
  5. dry with materialthe combined organic extracts were dried over magnesium sulfate
  6. customfollowed by evaporation

Sources & evidence

ORD record
ord-ab962237bb5a43258b12f5e71034349b
Source dataset
uspto-grants-2015_06
Patent number
US09051354B2

Reaction notes

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