m-Chloroperbenzoic acid → HCID 13982960, compound

HRID 649220Notes

Reaction equation

HRID 649220 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]2[N:7]=[C:8]([S:10][CH2:11][C:12]3[C:17]([O:18][CH3:19])=[C:16]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])[CH:15]=[CH:14][N:13]=3)[NH:9][C:5]=2[CH:4]=1.ClC1C=CC=C(C(OO)=[O:36])C=1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]2[N:7]=[C:8]([S:10]([CH2:11][C:12]3[C:17]([O:18][CH3:19])=[C:16]([O:20][CH2:21][C:22]([F:23])([F:25])[F:24])[CH:15]=[CH:14][N:13]=3)=[O:36])[NH:9][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13982955HCID 13982955, compound

Product 1

HCID 13982960HCID 13982960, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

5-Methoxy-2-[[3-methoxy-4-(2,2,2-trifluoroethoxy)pyrid-2-yl]methylthio]benzimidazole (989 mg) was dissolved in chloroform (30 ml), to which a solution of m-chloroperbenzoic acid (503 mg) in chloroform (8 ml) was added dropwise under ice-cooling over 5 minutes. The reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and then a saturated saline, and dried with anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by column chromatography, to give 5-methoxy-2-[[3-methoxy-4-(2,2,2-trifluoroethoxy)pyrid-2-yl)methylsulfinyl]benzimidazole (712 mg) as a light brownish yellow powder. m.p. 36°-46° C.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling over 5 minutes
  3. washThe reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materiala saturated saline, and dried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c0528f99b79745eb8301ef22c90254af
Source dataset
uspto-grants-1988_04
Patent number
US04738975

Reaction notes

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