m-Chloroperbenzoic acid → HCID 13749938, compound

HRID 622159Notes

Reaction equation

HRID 622159 reaction equation
[CH3:1][C:2]1[C:3]([CH2:17][S:18][C:19]2[NH:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[N:23]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12].ClC1C=CC=C(C(OO)=[O:36])C=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:3]([CH2:17][S:18]([C:19]2[NH:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[N:20]=2)=[O:36])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:16])([F:15])[C:11]([F:12])([F:14])[F:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13654767HCID 13654767, compound

Product 1

HCID 13749938HCID 13749938, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 2-[[3-methyl-4-(2,2,3,3,3-pentafluoropropoxy)-2-pyridyl]methylthio]benzimidazole (2.2 g) in chloroform (20 ml), a solution of m-chloroperbenzoic acid (*1.3 g) in chloroform (15 ml) was added dropwise while ice-cooling over a period of 30 minutes and the resulting reaction mixture was washed with a saturated aqueous sodium hydrogen carbonate. After drying over magnesium sulfate, the solvent was concentrated. The residue was applied on a silica gel (50 g) column, eluted with ethyl acetate and then recrystallized from acetone-isopropyl ether to give 1.78 g of 2-[[3-methyl-4-(2,2,3,3,3-pentafluoropropoxy)-2-pyridyl]methylsulfinyl]benzimidazole as pale yellow prisms. Melting point: 161°~163° C. (decomposition).

Workup

  1. temperaturecooling over a period of 30 minutes
  2. customthe resulting reaction mixture
  3. washwas washed with a saturated aqueous sodium hydrogen carbonate
  4. dry with materialAfter drying over magnesium sulfate
  5. concentrationthe solvent was concentrated
  6. washeluted with ethyl acetate
  7. customrecrystallized from acetone-isopropyl ether

Sources & evidence

ORD record
ord-7da9c7799c8040018d4d377cfd766044
Source dataset
uspto-grants-1988_09
Patent number
US04769456

Reaction notes

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