Sodium Azide → 1-(Azidomethyl)-4-methoxybenzene
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)C=O.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
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 23 °C
Procedure
To a stirred solution of 4-methoxybenzyl chloride (25.0 g, 156 mmol) in N,N-dimethylformamide (75 mL) was added sodium azide (11.5 g, 177 mmol). The reaction mixture was stirred at 23° C. for 15 h, then diluted with water (300 mL). The mixture was extracted with diethyl ether (3×75 mL) and the combined organic layers were washed with water (2×100 mL). The organic layer was dried (MgSO4), filtered, and evaporated under reduced pressure to afford the title compound (25.5 g) as a pale yellow oil. The title compound was used directly in the next step without further purification.
Workup
- extractionThe mixture was extracted with diethyl ether (3×75 mL)
- washthe combined organic layers were washed with water (2×100 mL)
- dry with materialThe organic layer was dried (MgSO4)
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-909280a2f57c47a4ac67aa2e45772146
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09302999B2
Reaction notes
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