Water → HCID 22024556, compound

HRID 501017Notes

Reaction equation

HRID 501017 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([CH:15]=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][N:14]=1.F[B-](F)(F)F.[O:24]=[N+:25]=[O:26].O>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([C:15]([N+:25]([O-:26])=[O:24])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11073463Nitronium tetrafluoroborateHCID 22024485HCID 22024485, compound

Product 1

HCID 22024556HCID 22024556, compoundYield 1,323.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

8-(2,4-Dichlorophenyl)-2-methylimidazo[1,2-a]pyrazine (0.10 g, 0.36 mmol) was dissolved in acetonitrile (0.36 mL), then nitronium tetrafluoroborate (72 mg, 0.54 mmol) was added thereto, and the mixture was stirred at room temperature for 1 hour under nitrogen atmosphere. Water was added to the reaction mixture, and it was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3) to give 8-(2,4-dichlorophenyl)-2-methyl-3-nitroimidazo[1,2-a]pyrazine (1.54 g) as a yellow oil.

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-66046cee6c0c4b9f9717aa1f66589fad
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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