Ethyl Acetate → HCID 66968962, compound

HRID 2095787Notes

Reaction equation

HRID 2095787 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N+:9]=2[O-])=[CH:4][CH:3]=1.C[Si]([C:20]#[N:21])(C)C.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>O1CCCC1.CN(C)C(Cl)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:20]#[N:21])[CH:11]=[CH:12][C:13]=2[CH3:14])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 58158491Pyridine, 2-(4-fluorophenyl)-3-methyl-, 1-oxide

Product 1

HCID 66968962HCID 66968962, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6598Dimethylcarbamoyl ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-3-methylpyridine 1-oxide (24 g, 0.118 mol) in tetrahydrofuran (200 mL) were added trimethylsilyl cyanide (19.2 mL, 0.153 mol) and dimethylcarbamoyl chloride (14.1 mL, 0.153 mmol), and the mixture was heated under reflux for 2 hr. Ethyl acetate and saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The obtained residue was washed with diethyl ether and collected by filtration to give the title compound (16.7 g, 67%) as a white solid. Under reduced pressure, the filtrate was concentrated, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9) to give the title compound (3.0 g, 12%) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. extractionthe mixture was extracted 3 times with ethyl acetate
  4. washThe combined organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. washThe obtained residue was washed with diethyl ether
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-4dc3b516af8d4bd69533e8fa2be28354
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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