m-Chloroperbenzoic acid → Methyl 2-fluoro-4-[3-(methylsulfinyl)-1,2,4-triazin-6-yl]benzoate

HRID 607608Notes

Reaction equation

HRID 607608 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([C:12]2[N:17]=[N:16][C:15]([S:18][CH3:19])=[N:14][CH:13]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].ClC1C=CC=C(C(OO)=[O:28])C=1>C(Cl)Cl>[F:1][C:2]1[CH:11]=[C:10]([C:12]2[N:17]=[N:16][C:15]([S:18]([CH3:19])=[O:28])=[N:14][CH:13]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59216327Methyl 2-fluoro-4-[3-(methylthio)-1,2,4-triazin-6-yl]benzoate

Product 1

HCID 59216280Methyl 2-fluoro-4-[3-(methylsulfinyl)-1,2,4-triazin-6-yl]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a cooled (0° C.) solution of methyl 2-fluoro-4-[3-(methylthio)-1,2,4-triazin-6-yl]benzoate (0.180 g, 0.000644 mol) in methylene chloride (10 mL) was added m-chloroperbenzoic acid (0.32 g, 0.0014 mol) in DCM (3 ml) with stirring. The mixture was stirred at 0° C. for 1.5 h, and diluted with DCM. The resulting solution was quenched with saturated Na2S2O3 solution. After separation the organic layer was washed with saturated NaHCO3 solution, brine; and dried over Na2SO4. After filtration the filtrate was concentrated to yield nearly quantitative product which was directly used in the next step without further purification. Analytical LCMS: (M+H)+=296.0.

Workup

  1. stirringThe mixture was stirred at 0° C. for 1.5 h
  2. customThe resulting solution was quenched with saturated Na2S2O3 solution
  3. customAfter separation the organic layer
  4. washwas washed with saturated NaHCO3 solution, brine
  5. dry with materialand dried over Na2SO4
  6. filtrationAfter filtration the filtrate
  7. concentrationwas concentrated
  8. customto yield nearly quantitative product which
  9. customwas directly used in the next step without further purification

Sources & evidence

ORD record
ord-9f75e4df373f4903aed9afeb1bdf4449
Source dataset
uspto-grants-2011_03
Patent number
US07915408B2

Reaction notes

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