m-Chloroperbenzoic acid → HCID 178439108, compound

HRID 379930Notes

Reaction equation

HRID 379930 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][S:7][C@@H:8]2[CH2:13][O:12][C@@H:11](/[C:14](/[CH3:26])=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[O:10][CH2:9]2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:37])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][S:7]([C@@H:8]2[CH2:9][O:10][C@@H:11](/[C:14](/[CH3:26])=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:23])[F:25])=[CH:18][CH:17]=3)[O:12][CH2:13]2)=[O:37])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178439107HCID 178439107, compound

Product 1

HCID 178439108HCID 178439108, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 10 ml of methylene chloride were dissolved 382 mg (0.89 mmol) of trans-5-[(4-chlorobenzyl)thio]-2-[(E)-1-methyl-2-[4-(trifluoromethyl)phenyl]vinyl]-1,3-dioxane, and 188 mg (0.92 mmol) of m-chloroperbenzoic acid (purity: 85%) were added to the solution, followed by stirring of the resulting mixture for 15 minutes. The reaction mixture was washed with an aqueous sodium hydrogencarbonate solution and the solid obtained by evaporation of the solvent was washed with a mixed solvent of ethyl acetate-hexane to obtain 328 mg (yield: 83%) having a melting point of 192 to 194° C.

Workup

  1. additionwere added to the solution
  2. washThe reaction mixture was washed with an aqueous sodium hydrogencarbonate solution
  3. customthe solid obtained by evaporation of the solvent
  4. washwas washed with a mixed solvent of ethyl acetate-hexane
  5. customto obtain 328 mg (yield: 83%)

Sources & evidence

ORD record
ord-0c81d25773894cbb8979a6200dc3435b
Source dataset
uspto-grants-2001_10
Patent number
US06300357B1

Reaction notes

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