Thionyl Chloride → HCID 86645104, compound

HRID 658347Notes

Reaction equation

HRID 658347 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[C:4]([C:12](O)=[O:13])[C:3]1=[O:15].S(Cl)([Cl:18])=O>>[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[C:4]([C:12]([Cl:18])=[O:13])[C:3]1=[O:15]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 68494030HCID 68494030, compound

Product 1

HCID 86645104HCID 86645104, compound

Procedure

1,2-dihydro-1-methyl-2-oxo-6-(trifluoromethyl)pyridine-3-carboxylic acid (11.2 g, 50.6 mmol) was dissolved in thionyl chloride (70 mL), and the mixture was refluxed for 2 hours. The reaction solution was concentrated under reduced pressure to obtain 1,2-dihydro-1-methyl-2-oxo-6-(trifluoromethyl)pyridine-3-carbonyl chloride. The obtained acid chloride was dissolved in acetonitrile (80 mL), and added dropwise to a mixed solution of 1,3-cyclohexanedione (4.98 g, 44.4 mmol), triethylamine (5.4 g, 53.3 mmol) and acetonitrile (20 mL), under ice cooling. After the stirring for a day at room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. After separating the inorganic substance by filtration, the solvent was distilled off under reduced pressure, and thus obtained crystal was washed with diisopropylether, to obtain 14.5 g of a subject compound (yield: 90.5%).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-664fef61fbc744aea0bed2308e39d79f
Source dataset
uspto-grants-2011_12
Patent number
US08076487B2

Reaction notes

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