Phosphorus oxychloride → HCID 117770690, compound

HRID 1526314Notes

Reaction equation

HRID 1526314 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([CH:8]([CH:10]([CH3:12])[CH3:11])[CH3:9])[C:4](=[O:13])[C:3]=1[CH:14]=[N:15]O.P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([CH:8]([CH:10]([CH3:11])[CH3:12])[CH3:9])[C:4](=[O:13])[C:3]=1[C:14]#[N:15]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 117770397HCID 117770397, compound

Product 1

HCID 117770690HCID 117770690, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-chloro-3-((hydroxyimino)methyl)-1-(3-methylbutan-2-yl)pyridin-2(1H)-one obtained in Step D (328 mg) in acetonitrile (3.0 mL) was added phosphorus oxychloride (0.126 mL) at room temperature. The reaction mixture was heated at 90° C. for 30 min, and cooled to room temperature. The reaction mixture was poured into ice water, and the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (305 mg).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-73dde49451d0444181496e8f7169e99d
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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