m-Chloroperbenzoic acid → 3-(2-Fluorophenyl)-5-(methanesulfinyl)-4-methyl-4H-1,2,4-triazole

HRID 703132Notes

Reaction equation

HRID 703132 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([CH3:13])[C:11]([S:14][CH3:15])=[N:10][N:9]=1.ClC1C=C(C=CC=1)C(OO)=[O:21]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([CH3:13])[C:11]([S:14]([CH3:15])=[O:21])=[N:10][N:9]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 30879983-(2-Fluorophenyl)-4-methyl-5-(methylsulfanyl)-4H-1,2,4-triazole

Product 1

HCID 30880003-(2-Fluorophenyl)-5-(methanesulfinyl)-4-methyl-4H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred, 0° C., solution of 3-(2-fluorophenyl)-4-methyl-5-methylthio-4H-1,2,4-triazole (5.0 g, 2.2×10-2 mole) and CH2Cl2 (125 ml) was added portionwise m-chloroperoxybenzoic acid (12.1 g, 5.6×10-2 mole, 80% active MCPBA). After stirring overnight at room temperature, the reaction was diluted with CH2Cl2 until homogeneous and was then washed in turn twice with saturated aqueous NaHCO3 and once with saturated aqueous NaCl. After drying over anhydrous Na2SO4, the CH2Cl2 was evaporated at reduced pressure leaving a solid which was purified by chromatography and subsequent crystallization from EtOAc/hexane giving colorless matted needles: 3.6 (63%), mp 128°-130° C.

Workup

  1. washwas then washed
  2. dry with materialAfter drying over anhydrous Na2SO4
  3. customthe CH2Cl2 was evaporated at reduced pressure
  4. customleaving a solid which
  5. customwas purified by chromatography and subsequent crystallization from EtOAc/hexane giving colorless matted needles

Sources & evidence

ORD record
ord-e6e5be09a0784c51b19c0fd56a3ee25f
Source dataset
uspto-grants-1991_01
Patent number
US04981863

Reaction notes

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