m-Chloroperbenzoic acid → 2-Methylsulfinyl-4-difluoromethoxy-6-methylpyrimidine

HRID 1719786Notes

Reaction equation

HRID 1719786 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][S:13][C:14]1[N:19]=[C:18]([O:20][CH:21]([F:23])[F:22])[CH:17]=[C:16]([CH3:24])[N:15]=1>C(Cl)Cl>[CH3:12][S:13]([C:14]1[N:19]=[C:18]([O:20][CH:21]([F:23])[F:22])[CH:17]=[C:16]([CH3:24])[N:15]=1)=[O:6]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 6943822-Methylthio-4-difluoromethoxy-6-methylpyrimidine

Product 1

HCID 134918262-Methylsulfinyl-4-difluoromethoxy-6-methylpyrimidineYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A suspension of 20.6 g (0.1 mol) of 3-chloroperoxybenzoic acid in 100 ml of methylene chloride is cooled to a temperature of between -15° C. and -20° C., and there is then added dropwise a solution of 20.6 g (0.1 mol) of 2-methylthio-4-difluoromethoxy-6-methylpyrimidine in 50 ml of methylene chloride. After the reaction mixture has been stirred for 1 hour at the same temperature, it is diluted with methylene chloride; it is subsequently washed with a sodium hydrogen carbonate solution and water, dried over sodium sulfate and concentrated by evaporation. Crystallisation of the residue from a methylene chloride/petroleum ether mixture yields 21.6 g (97% of theory) of 2-methylsulfinyl-4-difluoromethoxy-6-methylpyrimidine, m.p. 105°-107° C.

Workup

  1. temperatureis cooled to a temperature of between -15° C. and -20° C., and there
  2. washit is subsequently washed with a sodium hydrogen carbonate solution and water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customCrystallisation of the residue from a methylene chloride/petroleum ether mixture

Sources & evidence

ORD record
ord-91e088f261b74cc59606b13ba1fa2f35
Source dataset
uspto-grants-1985_09
Patent number
US04542216

Reaction notes

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