Water → HCID 21928381, compound

HRID 1243623Notes

Reaction equation

HRID 1243623 reaction equation
[N:1]([CH2:4][CH2:5][CH:6]([OH:14])[C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9])=[N+:2]=[N-:3].Cl[C:16]1[N:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:17]=1[C:18]#[N:19].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[N:1]([CH2:4][CH2:5][CH:6]([O:14][C:16]1[N:23]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:21]=[CH:20][C:17]=1[C:18]#[N:19])[C:7]([F:12])([F:13])[C:8]([F:10])([F:11])[F:9])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27784132-Chloro-6-(trifluoromethyl)nicotinonitrileHCID 21928374HCID 21928374, compound

Product 1

HCID 21928381HCID 21928381, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-azido-1,1,1,2,2-pentafluoro-3-pentanol (500 mg, 2.28 mmol) in dimethylformamide (10 ml) was added 2-chloro-6-(trifluoromethyl)nicotinonitrile (565 mg, 2.74 mmol) followed by caesium carbonate (2.20 g, 6.75 mmol). The reaction mixture turned brown. After 2 h, the reaction mixture was added to water (10 ml) and extracted with diethyl ether (2×15 ml). The combined organics were washed with brine (20 ml) and dried over anhydrous sodium sulfate. Removal of the solvents yielded a brown liquid. Purification by silica gel chromatography using hexanes/ethyl acetate (10:1 then 1:1) gave the title compound as a yellow liquid (780 mg, 88%).

Workup

  1. extractionextracted with diethyl ether (2×15 ml)
  2. washThe combined organics were washed with brine (20 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customRemoval of the solvents
  5. customyielded a brown liquid
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-e5eb00e3bf1f4465907776a6e3ccb85b
Source dataset
uspto-grants-2006_10
Patent number
US07119109B2

Reaction notes

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