m-Chloroperbenzoic acid → HCID 15057075, compound

HRID 892727Notes

Reaction equation

HRID 892727 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7](=[O:18])[NH:8][CH2:9][CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.C1C=C(Cl)C=C(C(OO)=[O:27])C=1>C(Cl)Cl>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7](=[O:18])[NH:8][CH2:9][CH2:10][S:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)=[O:27]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14441150HCID 14441150, compound

Product 1

HCID 15057075HCID 15057075, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.0 g (7.54 mmol) of 2-oxo-1-[[2-(pyridin-2-ylthio)ethyl]carbamoyl]pyrrolidine in 35 ml of CH2Cl2 was added 1.63 g (7.54 mmol) of m-CPBA (content 80%) under ice-cooling. Then the mixture was stirred for 1.5 hr. at room temperature. The reaction solution was washed with aqueous NaHCO3 and water. After drying, the solvent was removed by evaporration. The residue was refined by silica gel column chromatography, then the crystalline objective compound was obtained from the eluate with benzene/ethyl acetate (3/1-1/1 v/v). The compound was washed with Et2O and collected by filtration, whereby 0.93 g of the crystalline compound (Ib-3) melting at 119.5°-120.5° C. was obtained. Yield: 43.9%.

Workup

  1. temperaturecooling
  2. customat room temperature
  3. washThe reaction solution was washed with aqueous NaHCO3 and water
  4. customAfter drying
  5. customthe solvent was removed by evaporration
  6. customthe crystalline objective compound was obtained from the eluate with benzene/ethyl acetate (3/1-1/1 v/v)
  7. washThe compound was washed with Et2O
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a9c7aefa960b48a086e1fd7f131b4405
Source dataset
uspto-grants-1992_06
Patent number
US05120733

Reaction notes

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