Water → HCID 53729649, compound

HRID 1646231Notes

Reaction equation

HRID 1646231 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH:10]=[CH:11][C:12]2[CH:13]=[CH:14][C:15]([O:21][CH2:22][O:23][CH3:24])=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:33])C=1.[OH2:36]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:9][CH:10]=[CH:11][C:12]2[CH:13]=[CH:14][C:15]([O:21][CH2:22][O:23][CH3:24])=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=2)(=[O:33])=[O:36])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 53650486HCID 53650486, compound

Product 1

HCID 53729649HCID 53729649, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a current of argon, a solution of 300 mg of 5-[3-(4-chlorophenylthio)-1-propenyl]-2-methoxymethoxy nitrobenzene in 6 ml of methylene chloride and 283 mg of m-chloroperbenzoic acid added thereto as kept cooled with ice were stirred for eight hours. The reaction mixture was combined with water and extracted from ethyl acetate. The consequently separated organic layer was washed sequentially with a saturated aqueous sodium hydrogen carbonate solution and saturated saline solution in the order mentioned and then dried with anhydrous sodium sulfate. The residue from drying was concentrated under a vacuum and the concentrate was subjected to silica gel column chromatography. From the hexane-ethyl acetate (2:1 V/V) eluate, 240 mg of 5-[3-(4-chlorophenylsulfonyl)-1-propenyl]-2-methoxymethoxy nitrobenzene was obtained in the form of yellow crystals. The yield was 74%.

Workup

  1. temperatureas kept cooled with ice
  2. extractionextracted from ethyl acetate
  3. washThe consequently separated organic layer was washed sequentially with a saturated aqueous sodium hydrogen carbonate solution and saturated saline solution in the order
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe residue from drying
  6. concentrationwas concentrated under a vacuum

Sources & evidence

ORD record
ord-f4d6fdd99e084967b3ec4855317a3c51
Source dataset
uspto-grants-1993_01
Patent number
US05179105

Reaction notes

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