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

HRID 877355Notes

Reaction equation

HRID 877355 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C.O>[N:11]([CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[N+:12]=[N-:13]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 109317671-(Azidomethyl)-4-methoxybenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of p-methoxybenzyl chloride (4.26 mL, 31.4 mmol) in DMF (20 mL) was added sodium azide (2.04 g, 31.4 mmol). The reaction mixture was stirred at room temperature for 48 hours, diluted with H2O (200 mL), and then extracted with ether. The combined organic layers were washed w/H2O, dried over Na2SO4, filtered and conc. The clear oil obtained (4.9 g, 96%) was pure enough to use. 1H NMR (CDCl3, 400 MHz) 7.26-7.23 (m, 2H); 6.93-6.89 (m, H); 4.27 (s, 2H); 3.82 (s, 3H).

Workup

  1. extractionextracted with ether
  2. washThe combined organic layers were washed w/H2O
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customconc. The clear oil obtained (4.9 g, 96%)

Sources & evidence

ORD record
ord-008e6139fb184f0ebc8a276ea578bbd8
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

Loading…