Sodium Azide → 2-Azido-6-(trifluoromethyl)pyridine
Reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[N:3]=1.[N-:12]=[N+:13]=[N-:14].[Na+]>CS(C)=O>[N:12]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[N:3]=1)=[N+:13]=[N-:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 82.5 grams (g) of 2-fluoro-6-(trifluoromethyl)pyridine (0.5 mole), 65 g of sodium azide (1.0 mole) and 400 milliliters (ml) of dimethylsulfoxide (DMSO) was heated to a temperature of 80° C. for 18 hours. The mixture was allowed to cool and then poured into 1500 ml of ice water. This resulting mixture was then extracted 4 times with 300 ml of pentane each time. The pentane extracts were combined, washed with 500 ml of a saturated NaCl solution and dried with MgSO4. The pentane was then carefully evaporated leaving 67 g of the desired 2-azido-6-(trifluoromethyl)pyridine as a light yellow oil having an RI of 1.4771 @25° C.
Workup
- temperatureto cool
- extractionThis resulting mixture was then extracted 4 times with 300 ml of pentane each time
- washwashed with 500 ml of a saturated NaCl solution
- dry with materialdried with MgSO4
- customThe pentane was then carefully evaporated
Sources & evidence
- ORD record
- ord-7c2ea18d086e4449a14490cefb97f66f
- Source dataset
- uspto-grants-1984_10
- Patent number
- US04474599
Reaction notes
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