Toluene → HCID 86645106, compound

HRID 658351Notes

Reaction equation

HRID 658351 reaction equation
C1(C)C=CC=CC=1.S(Cl)([Cl:10])=O.[O:12]=[C:13]1[C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=[C:15]([C:22]([F:25])([F:24])[F:23])[N:14]1[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[O:12]=[C:13]1[C:18]([C:19]([Cl:10])=[O:20])=[CH:17][CH:16]=[C:15]([C:22]([F:25])([F:24])[F:23])[N:14]1[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 68495428HCID 68495428, compound

Product 1

HCID 86645106HCID 86645106, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Toluene (20 mL), thionyl chloride (1.3 g, 10.7 mmol) and a catalytic amount of N,N′-dimethylformamide were added to 1,2-dihydro-2-oxo-1-phenylmethyl-6-(trifluoromethyl)pyri-dine-3-carboxylic acid (2.0 g, 7.2 mmol), and the mixture was refluxed for 2 hours. The reaction mixture was concentrated under reduced pressure to obtain 1,2-dihydro-2-oxo-1-phenylmethyl-6-(trifluoromethyl)pyridine-3-carbonyl chloride. The obtained acid chloride was dissolved in acetonitrile (30 mL), and 1,3-cyclohexanedione (0.9 g, 7.9 mmol) and sodium cyanide (0.8 g, 15.8 mmol) were added thereto. This mixture was stirred 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 concentrated solution was purified by column chromatography, to obtain 1.5 g of a desired product (yield: 68%).

Workup

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

Sources & evidence

ORD record
ord-8a3abffba85d4b10973a56bcd50c9f0e
Source dataset
uspto-grants-2011_12
Patent number
US08076487B2

Reaction notes

Loading…