Acetone → 4-(4-Chlorophenyl)-2-(methylsulfonyl)pyrimidine

HRID 33444Notes

Reaction equation

HRID 33444 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10](SC)[N:9]=2)=[CH:4][CH:3]=1.O[O:17][S:18]([O-:20])=O.[K+].[CH3:22]C(C)=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([S:18]([CH3:22])(=[O:20])=[O:17])[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 28211934-(4-Chlorophenyl)-2-(methylthio)pyrimidineHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 219059934-(4-Chlorophenyl)-2-(methylsulfonyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 4-(4-chlorophenyl)-2-methylthiopyrimidine (1.1 g, 4.65 mmol) in acetone (30 ml) and water (10 ml) was added oxone (7.14 g, 11.62 mmol). The reaction mixture was stirred for 18 hours then diluted with water and extracted into dichloromethane. The extracts were dried over magnesium sulfate, filtered and concentrated to provide a white solid: EI-MS (m/z) 269 [M+1]+.

Workup

  1. extractionextracted into dichloromethane
  2. dry with materialThe extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto provide a white solid

Sources & evidence

ORD record
ord-1833d5fec08f45d4815103b7e5e17d93
Source dataset
uspto-grants-2008_09
Patent number
US07429599B2

Reaction notes

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