Acetone → HCID 15541009, compound

HRID 2185836Notes

Reaction equation

HRID 2185836 reaction equation
CS[C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([C:26]#[N:27])[C:12](=[O:25])[NH:13][C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH:6]=[CH:5][N:4]=1.O[O:29][S:30]([O-:32])=O.[K+].[CH3:34]C(C)=O>CO.O>[CH3:34][S:30]([C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([C:26]#[N:27])[C:12](=[O:25])[NH:13][C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH:6]=[CH:5][N:4]=1)(=[O:32])=[O:29]

Participants

6

Reactant 3

HCID 180AcetoneHCID 22452602HCID 22452602, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 15541009HCID 15541009, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5-(2-methylsulfanylpyrimidin-4-yl)-2-oxo-6-(3-trifluoromethylphenyl)-1,2-dihydropyridine-3-carbonitrile (0.40 gm, 0.00104 mole) in methanol (40 mL) was slowly added a solution of Oxone (1.90 gm, 0.0030 mole) in water (40 mL). The mixture was allowed to stir for 30 minutes and then acetone (20 mL) added. The reaction was then stirred for 48 hrs, and then concentrated to remove the acetone and methanol. The resulting mixture was dissolved in ethyl acetate and water and the pH adjusted to 7.0 with 10% aqueous sodium hydrogen sulfate. The ethyl acetate layer was removed and aqueous layer washed with ethyl acetate. The ethyl acetate extracts were dried over sodium sulfate and concentrated to give 0.25 gm (57%) of the title compound.

Workup

  1. stirringThe reaction was then stirred for 48 hrs
  2. concentrationconcentrated
  3. customto remove the acetone and methanol
  4. dissolutionThe resulting mixture was dissolved in ethyl acetate
  5. customThe ethyl acetate layer was removed
  6. washaqueous layer washed with ethyl acetate
  7. dry with materialThe ethyl acetate extracts were dried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dd5d0449f6fc48feb84f0aa4744cbbf4
Source dataset
uspto-grants-2002_06
Patent number
US06403596B1

Reaction notes

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