Benzenesulfonyl chloride → 1-(phenylsulfonyl)-2-pyrrolidinone

HRID 1762458Notes

Reaction equation

HRID 1762458 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si](C)(C)[N:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18]>>[C:1]1([S:7]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 844611-(Trimethylsilyl)pyrrolidin-2-one

Product 1

HCID 6676021-(phenylsulfonyl)-2-pyrrolidinoneYield 37.1%

Procedure

To 7.06 g of benzenesulfonyl chloride (0.04 mole) was added 6.9 g of N-trimethylsilyl-2-pyrrolidone (0.044 mole), and the mixture was stirred at the reflux temperature for 30 minutes. The reaction mixture was subjected to chromatography on a column (D 40 mm×L 250 mm) of 150 g of silica gel (Wako Gel C-200). Elution with a mixed solvent of hexane-ethyl acetate (3:2) gave a crystalline product, which was recrystallized from a mixed solvent of chloroform-ether to give 3.34 g of N-benzenesulfonyl-2-pyrrolidone as colorless crystals.

Workup

  1. washElution with a mixed solvent of hexane-ethyl acetate (3:2)
  2. customgave a crystalline product, which
  3. customwas recrystallized from a mixed solvent of chloroform-ether

Sources & evidence

ORD record
ord-fd9624f3a1354acb88ce143b21e751f0
Source dataset
uspto-grants-1989_05
Patent number
US04833156

Reaction notes

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