Acetic Acid → 2-Methanesulphonyl-4-(2,2,2-trifluorethoxy)-pyrimidine

HRID 917

Reaction equation

HRID 917 reaction equation
CS[C:3]1[N:8]=[C:7]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])[CH:6]=[CH:5][N:4]=1.[Mn]([O-])(=O)(=O)=O.[K+].[S:21](S([O-])=O)([O-:24])(=O)=[O:22].[Na+].[Na+].[C:30](O)(=O)C>O>[CH3:30][S:21]([C:3]1[N:8]=[C:7]([O:9][CH2:10][C:11]([F:14])([F:12])[F:13])[CH:6]=[CH:5][N:4]=1)(=[O:24])=[O:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516875Potassium PermanganateHCID 656671Sodium PyrosulfiteHCID 196941862-Methylthio-4-(2,2,2-trifluoroethoxy)pyrimidine

Product 1

HCID 196941792-Methanesulphonyl-4-(2,2,2-trifluorethoxy)-pyrimidineYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-methylthio-4-(2,2,2-trifluoroethoxy)pyrimidine (1.0 g) in glacial acetic acid (20 ml) at 15° C. was added a solution of potassium permanganate (2.4 g) in water (75 ml). When the addition was complete a solution of sodium metabisulphite (10% aqueous) was added until a clear solution was obtained. The reaction mixture was extracted with ether (3×70 ml), the combined extracts were washed with brine (3×), dried and concentrated to give 2-methanesulphonyl-4-(2,2,2-trifluorethoxy)-pyrimidine (1.0 g, 87% yield) as a clear oil; 1H NMR δ 3.35(3H,s); 4.91(2H,q); 7.11(1H.d); 8.69(1H,d) ppm.

Workup

  1. additionWhen the addition
  2. additionwas added until a clear solution
  3. customwas obtained
  4. extractionThe reaction mixture was extracted with ether (3×70 ml)
  5. washthe combined extracts were washed with brine (3×)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-47babce885794c6582621c55f5fc99d7
Source dataset
uspto-grants-1998_03
Patent number
US05723471

Linked notes

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