Sodium Azide → 9-Azidononanoic acid

HRID 1889147Notes

Reaction equation

HRID 1889147 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11].[N-:13]=[N+:14]=[N-:15].[Na+]>ClCCl>[N:13]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[N+:14]=[N-:15]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 5482219-Bromononanoic Acid

Product 1

HCID 152305499-Azidononanoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
60 °C

Procedure

9-bromononanoic acid (4a) (1.062 gr, 4.48 mmol) was dissolved in 15 mL of dry dichloromethane. Sodium azide (914 mg, 14 mmol) was then added and the mixture was stirred at 60° C. for 6 hours. The solution was cooled and diluted with 50 mL of dichloromethane and then washed with 1 M HCl (5×50 mL), brine (2×50 mL) and dried over magnesium sulfate. The mixture was then filtered and concentrated in vacuo to yield 90% of product 5a as a white solid. 1H-NMR (200 MHz, CDCl3): 1.3-1.5 (m; 8H), 1.5-1.7 (m; 4H), 2.33 (t; J=7.4 Hz; 2H), 3.25 (t; J=6.86 Hz; 2H).

Workup

  1. temperatureThe solution was cooled
  2. washwashed with 1 M HCl (5×50 mL), brine (2×50 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe mixture was then filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1572ea20b38b4b87b8a41b8a5e7b062f
Source dataset
uspto-grants-2013_08
Patent number
US08501969B2

Reaction notes

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