Sodium Azide → 3-Chloro-5-methoxybenzylazide

HRID 1715860Notes

Reaction equation

HRID 1715860 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1)[CH2:5]OS(C)(=O)=O.[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1)[CH2:5][N:16]=[N+:17]=[N-:18]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86631769HCID 86631769, compound

Product 1

HCID 577398023-Chloro-5-methoxybenzylazideYield 104.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methanesulfonic acid 3-chloro-5-methoxybenzyl ester (20 mmol, 5.01 g) in DMF (30 ml) was added NaN3 (60 mmol, 3.90 g). The mixture was stirred for 3 h and the contents subsequently separated between water (300 ml) and DCM (150 ml). The organic phase was washed with water (2×100 ml), then brine, and dried (MgSO4). Filtration and removal of solvents under reduced pressure yielded a yellow liquid (4.14 g). Purification by means of flash chromatography (silica, hexane/ether gradient 0-50%) provided the title compound (3.65 g, 93%). 1H NMR (CDCl3, 500 MHz) δ 3.80 (s, 3H), 4.27 (s, 2H), 6.73 (s, 1H), 6.85 (s, 1H) and 6.89 (s, 1H).

Workup

  1. customthe contents subsequently separated between water (300 ml) and DCM (150 ml)
  2. washThe organic phase was washed with water (2×100 ml)
  3. dry with materialbrine, and dried (MgSO4)
  4. filtrationFiltration and removal of solvents under reduced pressure

Sources & evidence

ORD record
ord-bf7e0885bac34878ada0efb5f9c26f88
Source dataset
uspto-grants-2010_09
Patent number
US07799947B2

Reaction notes

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