Sodium Azide → Methyl 4-(azidomethyl)benzoate

HRID 1371538Notes

Reaction equation

HRID 1371538 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1>CS(C)=O>[N:1]([CH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 11240942Methyl 4-(azidomethyl)benzoateYield 98.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

8.13 g of sodium azide are added over 5 minutes to a solution of 5.73 g of methyl 4-(bromomethyl)benzoate in 30 ml of DMSO and the mixture is stirred for 3 hours 30 minutes at RT. The reaction mixture is extracted with ether, the organic phase is washed with water and with saturated NaCl solution and dried over Na2SO4, and the solvent is evaporated off under vacuum. 4.72 g of the expected product are obtained in the form of a colourless oil.

Workup

  1. extractionThe reaction mixture is extracted with ether
  2. washthe organic phase is washed with water and with saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-e3bb5b6f27604497964eb5092f74ffab
Source dataset
uspto-grants-2007_01
Patent number
US07157454B2

Reaction notes

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