Water → HCID 19789831, compound

HRID 1655988Notes

Reaction equation

HRID 1655988 reaction equation
[C:1]([C:5]1[N:6]=[CH:7][NH:8][C:9]=1[CH3:10])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:14]1[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][N:15]=1.O>CN(C)C=O>[C:1]([C:5]1[N:6]=[CH:7][N:8]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:22])[F:23])=[CH:16][N:15]=2)[C:9]=1[CH3:10])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 579674HCID 579674, compound

Product 1

HCID 19789831HCID 19789831, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.5 g (3.6 m mol) of 4-tert-butyl-5-methylimidazole in 5 ml of N,N-dimethyl formamide is added slowly 150 mg (3.7 m mol) of an oily sodium hydride (60%) while cooling with ice, followed by stirring at the same temperature for 20 minutes. After the reaction is completed, to the reaction mixture is added dropwise 0.71 g (3.6 m mol) of 2,3-dichloro-5-trifluoromethylpyridine, followed by stirring at room temperature for 9 hours. After the reaction is completed, the reacton mixture is poured into water, and extracted with ethyl acetate. Further, then the residue is washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained product is subjected to silica gel chromatography to give 4-tert-butyl-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-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 is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-378d16d602c14ba59f1fba0375368b14
Source dataset
uspto-grants-1993_10
Patent number
US05252590

Reaction notes

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