Sodium Azide → 2,2-Difluoro-2-(2-pyridyl)ethylazide

HRID 398364Notes

Reaction equation

HRID 398364 reaction equation
FC(F)(F)S(O[CH2:7][C:8]([F:16])([F:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)(=O)=O.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C.O>[F:15][C:8]([F:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[CH2:7][N:19]=[N+:20]=[N-:21]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 110662242,2-Difluoro-2-(2-pyridyl)ethyl trifluoromethanesulfonate

Product 1

HCID 118054052,2-Difluoro-2-(2-pyridyl)ethylazide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 105 mg (0.31 mmol) of 2,2-difluoro-2-(2-pyridyl)ethyl trifluoromethanesulfonate and 43 mg (0.66 mmol) of sodium azide in 1.0 mL of DMF was heated at 60° C. under Ar. After 1.5 h, the mixture was cooled to rt, diluted with water and extracted with two portions of ether. The combined organic layers were washed twice with water, brine and dried over MgSO4. The solvents were removed at reduced pressure and a bath temperature of 20° C. to give the title compound as a brown oil:

Workup

  1. extractionextracted with two portions of ether
  2. washThe combined organic layers were washed twice with water, brine
  3. dry with materialdried over MgSO4
  4. customThe solvents were removed at reduced pressure and a bath temperature of 20° C.

Sources & evidence

ORD record
ord-28647f88efce40969b6626cf0ac53900
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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