m-Chloroperbenzoic acid → 2-[(4-Difluoromethoxy-3-methyl-2-pyridyl)methylsulfinyl]benzimidazole

HRID 1033742Notes

Reaction equation

HRID 1033742 reaction equation
[F:1][CH:2]([F:22])[O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:10][S:11][C:12]2[NH:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)[C:5]=1[CH3:21].ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)(Cl)Cl.CO>[F:22][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:10][S:11]([C:12]2[NH:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[N:13]=2)=[O:31])[C:5]=1[CH3:21]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 152302322-[(4-Difluoromethoxy-3-methyl-2-pyridyl)methylthio]benzimidazole

Product 1

HCID 99277612-[(4-Difluoromethoxy-3-methyl-2-pyridyl)methylsulfinyl]benzimidazoleYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×

Procedure

In chloroform (20 ml) - methanol (10 ml) was dissolved 2-[(4-difluoromethoxy-3-methyl-2-pyridyl)methylthio]benzimidazole (2.0 g). To the solution was added dropwise, under ice-cooling, a solution of m-chloroperbenzoic acid (MCPBA) (80%, 1.5 g in chloroform (20 ml). The reaction mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate and water, in that order, then dried (MgSO4). The solvent was distilled off. The residual solid was subjected to a silica gel column chromatography. From the portion eluted with ethyl acetate - methanol (100:3, v/v), was obtained 2-[(4-difluoromethoxy-3-methyl-2-pyridyl)methylsulfinyl]benzimidazole (1.5 g, 71%). Recrystallization from ethyl acetate--ether gave colorless needles, m.p. 157°-158° C. (decomp.).

Workup

  1. additionTo the solution was added dropwise, under ice-
  2. temperaturecooling
  3. washThe reaction mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate and water, in that order
  4. dry with materialdried (MgSO4)
  5. distillationThe solvent was distilled off
  6. washFrom the portion eluted with ethyl acetate - methanol (100:3

Sources & evidence

ORD record
ord-f5a81a9fe09d485fb8ab2f11303b5ad3
Source dataset
uspto-grants-1994_05
Patent number
US05312824

Reaction notes

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