Acetic Acid → 2-Methylsulfonyl-4-difluoromethoxy-6-methylpyrimidine

HRID 1719784Notes

Reaction equation

HRID 1719784 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].CS[C:9]1[N:14]=[C:13]([O:15][CH:16]([F:18])[F:17])[CH:12]=[C:11]([CH3:19])[N:10]=1.[C:20](O)(=O)C.[S:24]([O-:27])(O)=[O:25].[Na+]>O.C(Cl)Cl.[O-2].[Mn+2].C1OCCOCCOCCOCCOCCOC1>[CH3:20][S:24]([C:9]1[N:14]=[C:13]([O:15][CH:16]([F:18])[F:17])[CH:12]=[C:11]([CH3:19])[N:10]=1)(=[O:27])=[O:25]

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 516875Potassium PermanganateHCID 6943822-Methylthio-4-difluoromethoxy-6-methylpyrimidineHCID 23665763Sodium Bisulfite

Product 1

HCID 134918212-Methylsulfonyl-4-difluoromethoxy-6-methylpyrimidineYield 95%

Reagents, catalysts & solvents 4

HCID 2855718-Crown-6CatalystHCID 160959Manganese oxideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 70.0 g (0.44 mol) of potassium permanganate in 700 ml of water is added dropwise to a solution of 30.9 g (0.15 mol) of 2-methylthio-4-difluoromethoxy-6-methylpyrimidine, 0.75 g of 18-crown-6-ether and 30 ml of glacial acetic acid in 1400 ml of methylene chloride. This mixture is stirred for 3 hours at a temperature of between 20° and 25° C., and sodium hydrogen sulfite solution is then added until the precipitated manganese oxide (MnO2) is dissolved. The organic phase of the reaction mixture is separated, washed with water, dried over sodium sulfate and concentrated by evaporation. There are thus obtained, as a colourless residue, 33.8 g (95% of theory) of 2-methylsulfonyl-4-difluoromethoxy-6-methylpyrimidine, m.p. 86°-88° C.

Workup

  1. dissolutionis dissolved
  2. customThe organic phase of the reaction mixture is separated
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-80ea54f8d12a4ee782a62a2444887519
Source dataset
uspto-grants-1985_09
Patent number
US04542216

Reaction notes

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