Chloroform → HCID 10743043, compound

HRID 1885614Notes

Reaction equation

HRID 1885614 reaction equation
[CH2:1]([N:8]([CH3:28])[C:9]([CH:11]([CH2:18]SC1C=CC(Cl)=C(Cl)C=1)[CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32](C(OO)=O)[CH:31]=1.[S:40]([O-:43])([O-])=[O:41].[Na+].[Na+].C(Cl)(Cl)[Cl:47]>>[CH2:1]([N:8]([CH3:28])[C:9]([CH:11]([CH2:18][S:40]([C:32]1[CH:33]=[CH:34][C:35]([Cl:47])=[C:30]([Cl:29])[CH:31]=1)(=[O:43])=[O:41])[CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6212ChloroformHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 19879356HCID 19879356, compound

Product 1

HCID 10743043HCID 10743043, compound

Conditions

Temperature
0 °C

Procedure

Into a solution of methyl 4-(N-benzyl-N-methylcarbamoyl)-5-(3,4-dichlorophenylthio)pentanoate (110 mg) in dry chloroform (4 ml) were added portions of m-chloroperbenzoic acid (80%, 160 mg) with stirring at 0° C. After stirring at room temperature for 4 hours, sodium sulfite was added. The reaction mixture was washed with a saturated sodium bicarbonate solution and water, dried over MgSO4, and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography on silica by developing with dichloromethane/diethyl ether (2:1) to give 100 mg of methyl 4-(N-benzyl-N-methylcarbamoyl)-5-(3,4-dichlorophenylsulfonyl)pentanoate as an oil.

Workup

  1. stirringAfter stirring at room temperature for 4 hours
  2. washThe reaction mixture was washed with a saturated sodium bicarbonate solution and water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative thin-layer chromatography on silica

Sources & evidence

ORD record
ord-f296ed8f452648108094122a770c94f8
Source dataset
uspto-grants-1992_09
Patent number
US05145869

Reaction notes

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