Sodium Azide → HCID 86658306, compound

HRID 1191695Notes

Reaction equation

HRID 1191695 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[N-:14]=[N+:15]=[N-:16].[Na+].C1OCCOCCOCCOCCOC1>O1CCOCC1>[N:14]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)=[N+:15]=[N-:16]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 3633615-Crown-5HCID 27339782-[4-(Bromomethyl)phenyl]propanoic acid

Product 1

HCID 86658306HCID 86658306, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(4-bromomethylphenyl)-proprionic acid (1.5 g) in 1,4-dioxane was added NaN3 (5 g) and 15-crown-5 (100 mg). The mixture was heated to 80° C. for 16 h, then cooled. The solvent was removed under reduced pressure, and the residue chromatographed on silica to yield 2-(4-azidomethylphenyl)-proprionic acid as an off white solid.

Workup

  1. temperaturecooled
  2. customThe solvent was removed under reduced pressure
  3. customthe residue chromatographed on silica

Sources & evidence

ORD record
ord-7c27ac156c024eeeb05e5226b4235da3
Source dataset
uspto-grants-2014_03
Patent number
US08680125B2

Reaction notes

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