Sodium Azide → Methyl 4-(azidomethyl)benzoate
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
Product 1
Reagents, catalysts & solvents 1
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
- extractionThe reaction mixture is extracted with ether
- washthe organic phase is washed with water and with saturated NaCl solution
- dry with materialdried over Na2SO4
- 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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