1-Butyl-3-methylimidazolium tetrafluoroborate → HCID 67974760, compound

HRID 1502463Notes

Reaction equation

HRID 1502463 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[C:4](N)[CH:5]=[N:6][C:7]=1[CH3:8].[B-](F)(F)(F)[F:12].N#[O+].F[B-](F)(F)F.C([N+]1C=CN(C)C=1)CCC>C(OCC)(=O)C>[Br:1][C:2]1[C:7]([CH3:8])=[N:6][CH:5]=[C:4]([F:12])[C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 27341781-Butyl-3-methylimidazolium tetrafluoroborateHCID 70606665-Bromo-4,6-dimethylpyridin-3-amineHCID 11137142Nitrilooxonium tetrafluoroborate

Product 1

HCID 67974760HCID 67974760, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-bromo-4,6-dimethyl-pyridin-3-amine (500 mg, 2.49 mmol) and nitrosyl tetrafluoroborate (445 mg, 3.73 mmol) in 1-butyl-3-methylimidazolium tetrafluoroborate (9.48 mL, 49.74 mmol) was heated at 60° C. for 2 hours (caution: exothermic). The reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (2×20 mL), and then saturated aqueous sodium bicarbonate (20 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to provide a residue that was purified by flash chromatography (4 g, Silica, 0-50% ethyl acetate in heptane). Desired fractions were combined and evaporated in vacuo to afford the title compound as pale yellow oil (220 mg, 43%), which was used in the next step without further purification.

Workup

  1. washwashed with water (2×20 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a residue that
  7. customwas purified by flash chromatography (4 g, Silica, 0-50% ethyl acetate in heptane)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-5d0061673eea48bbb736b6254903156e
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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