Thionyl Chloride → HCID 117770334, compound

HRID 1526402Notes

Reaction equation

HRID 1526402 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([C@H:8]([CH:10]([CH3:12])[CH3:11])[CH3:9])[C:4](=[O:13])[C:3]=1[CH:14]=[N:15]O.S(Cl)(Cl)=O>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([C@H:8]([CH:10]([CH3:11])[CH3:12])[CH3:9])[C:4](=[O:13])[C:3]=1[C:14]#[N:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 117770785HCID 117770785, compound

Product 1

HCID 117770334HCID 117770334, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-chloro-3-((hydroxyimino)methyl)-1-((2S)-3-methylbutan-2-yl)pyridin-2(1H)-one obtained in Step D (23.2 g) in acetonitrile (300 mL) was added dropwise thionyl chloride (13.9 mL), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and to the residue were added diisopropyl ether/ethyl acetate/hexane. The insoluble substance was removed by filtration, and the filtrate was concentrated under reduced pressure. To the residue was added ethyl acetate, and the mixture was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (14.6 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionto the residue were added diisopropyl ether/ethyl acetate/hexane
  3. customThe insoluble substance was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTo the residue was added ethyl acetate
  6. washthe mixture was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-29776703d4a6404d8632fde5bf0051bc
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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