Water → HCID 19789828, compound

HRID 1655986Notes

Reaction equation

HRID 1655986 reaction equation
[F:1][C:2]([F:16])([C:12]([F:15])([F:14])[F:13])[C:3]([F:11])([F:10])[C:4]1[N:5]=[CH:6][NH:7][C:8]=1[CH3:9].[H-].[Na+].Cl[C:20]1[C:25]([Cl:26])=[CH:24][C:23]([C:27]([F:30])([F:29])[F:28])=[CH:22][N:21]=1.O>CN(C)C=O>[Cl:26][C:25]1[C:20]([N:7]2[C:8]([CH3:9])=[C:4]([C:3]([F:11])([F:10])[C:2]([F:1])([F:16])[C:12]([F:14])([F:15])[F:13])[N:5]=[CH:6]2)=[N:21][CH:22]=[C:23]([C:27]([F:29])([F:28])[F:30])[CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 19789826HCID 19789826, compound

Product 1

HCID 19789828HCID 19789828, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.6 g (2.4 m mol) of 4-heptafluoropropyl-5-methylimidazole in 5 ml of N,N-dimethyl formamide was added slowly 100 mg (2.4 m mol) of an oily sodium hydride (60%) while cooling with ice, followed by stirring at the same temperature for 10 minutes. After the reaction was completed, to the reaction mixture was added dropwise 0.52 g (2.4 m mol) of 2,3-dichloro-5-trifluoromethylpyridine, followed by stirring at room temperature for 9 hours. After the reaction was completed, the reaction mixture was poured into water, and extracted with ethyl acetate. Further, then the residue was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained product was subjected to silica gel chromatography to give 0.4 g of 1-(3-chloro-5-trifluoromethylpyridin-2-yl)-4-heptafluoropropyl-5-methylimidazole.

Workup

  1. temperaturewhile cooling with ice
  2. stirringby stirring at room temperature for 9 hours
  3. extractionextracted with ethyl acetate
  4. washFurther, then the residue was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8670926c444e4638ab20299e6fc2bca0
Source dataset
uspto-grants-1993_10
Patent number
US05252590

Reaction notes

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