m-Chloroperbenzoic acid → HCID 178493774, compound

HRID 845514Notes

Reaction equation

HRID 845514 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][N:6]=[C:5]([CH2:11][S:12][C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([O:22][C:23]([F:28])([F:27])[CH:24]([F:26])[F:25])=[CH:21][C:15]=3[N:14]=2)[CH:4]=1.ClC1C=C(C=CC=1)C(OO)=[O:34]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][N:6]=[C:5]([CH2:11][S:12]([C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([O:22][C:23]([F:27])([F:28])[CH:24]([F:25])[F:26])=[CH:21][C:15]=3[N:14]=2)=[O:34])[CH:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178493768HCID 178493768, compound

Product 1

HCID 178493774HCID 178493774, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the product in methylene chloride is obtained by the procedure described in Example 2 by oxidation of 0.76 g of 2-[(4,5-dimethoxy-2-pyridyl)methylthio]-5-(1,1,2,2-tetrafluoroethoxy)-1H-benzimidazole with 19 ml of a 0.1M solution of m-chloroperoxybenzoic acid in 30 ml of methylene chloride at -40° C., after extraction. After drying the solution over magnesium sulfate, the drying agent is filtered off, the filtrate is concentrated and the residue is crystallized from methylene chloride/diisopropyl ether. 0.64 g (82% of theory) of the title compound is obtained in the form of colorless crystals of m.p. 160°-162° C. (decomp.).

Workup

  1. extractionafter extraction
  2. dry with materialAfter drying the solution over magnesium sulfate
  3. filtrationthe drying agent is filtered off
  4. concentrationthe filtrate is concentrated
  5. customthe residue is crystallized from methylene chloride/diisopropyl ether

Sources & evidence

ORD record
ord-fb452fa10f6f47d1b71b3a9855095567
Source dataset
uspto-grants-1988_07
Patent number
US04758579

Reaction notes

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