Sodium Azide → 1-(Azidomethyl)-4-methoxybenzene

HRID 2178990Notes

Reaction equation

HRID 2178990 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[N-:11]=[N+:12]=[N-:13].[Na+]>C(#N)C>[N:11]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1)=[N+:12]=[N-:13]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 109317671-(Azidomethyl)-4-methoxybenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(chloromethyl)-4-methoxybenzene (20.0 g, 128 mmol) and sodium azide (12.5 g, 192 mmol) in acetonitrile (255 mL) was refluxed for 5 h under N2 atmosphere. The mixture was filtered and concentrated in vacuo. The residue was diluted in DCM, washed with H2O and brine, dried over Na2SO4 and concentrated in vacuo to afford crude 1-(azidomethyl)-4-methoxybenzene. The residue was used for the next reaction without further purification.

Workup

  1. temperaturewas refluxed for 5 h under N2 atmosphere
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted in DCM
  5. washwashed with H2O and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ba61bcabb5ac4fda88231f7ab2649bb4
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

Loading…