Sodium Azide → HCID 178497409, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[N-:15]=[N+:16]=[N-:17].[Na+].Cl.C([NH+](CC)CC)C>CN1CCCC1=O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([C:13]2[NH:17][N:16]=[N:15][N:14]=2)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
Combine methyl 2-methoxy-5-cyanobenzoate (0.67 mmol), sodium azide (0.13 g, 2.04 mmol), and triethylammonium hydrochloride (0.14 g, 1.03 mmol) in N-methylpyrrolidinone (6 mL). Heat to 150° C. After 4 hours, cool to ambient temperature and partition the reaction mixture between water and ethyl acetate. Separate the layers and extract the aqueous layer three times with ethyl acetate. Adjust the pH of the aqueous layer to about 1 using a 1M aqueous hydrochloric acid solution, The aqueous layer is again extracted three times with ethyl acetate, and twice with dichloromethane. The aqueous layer is saturated with sodium chloride and again extracted four times with dichloromethane. Combine the organic layers, dry over MgSO4, filter, and evaporate in vacuo to give methyl 2-methoxy-5-(1H-tetrazol-5-yl)benzoate.
Workup
- temperaturecool to ambient temperature
- custompartition the reaction mixture between water and ethyl acetate
- customSeparate the layers
- extractionextract the aqueous layer three times with ethyl acetate
- extractionThe aqueous layer is again extracted three times with ethyl acetate
- extractionagain extracted four times with dichloromethane
- dry with materialdry over MgSO4
- filtrationfilter
- customevaporate in vacuo
Sources & evidence
- ORD record
- ord-0d63c54bf2ad42089be929d068d4b293
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05977139
Reaction notes
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