Thiophenol → 1-(Phenylthio)pyrrolidine-2,5-dione

HRID 260476Notes

Reaction equation

HRID 260476 reaction equation
Cl[N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[C:9]1([SH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)Cl>[C:9]1([S:15][N:2]2[C:6](=[O:7])[CH2:5][CH2:4][C:3]2=[O:8])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 31398Chlorosuccinimide2×

Product 1

HCID 3617741-(Phenylthio)pyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a partial solution of N-chlorosuccinimide (3.34 g, 25 mmol) in dry methylene chloride (30 mL), cooled in an ice bath and under an inert atmosphere, was added thiophenol (2.05 mL, 20 mmol) via syringe. After stirring for 1 hour, additional N-chlorosuccinimide (0.40 g, 3 mmol) was added. After 2.5 hours total, triethylamine (3.9 mL, 28 mmol) was added dropwise. Within 15 minutes the reaction mixture was diluted with methylene chloride, the solvent washed with dilute aq. HCl and the solvent then dried (Na2SO4), filtered through a pad of charcoal and evaporated. The residue was triturated with diethyl ether and the product collected by filtration to yield the title compound mp 115°-116° C. [lit. mp 115°-116° C., J. Org. Chem., 34, 51 (1969)]. This material was used as is.

Workup

  1. waitAfter 2.5 hours total
  2. washthe solvent washed with dilute aq. HCl
  3. dry with materialthe solvent then dried (Na2SO4)
  4. filtrationfiltered through a pad of charcoal
  5. customevaporated
  6. customThe residue was triturated with diethyl ether
  7. filtrationthe product collected by filtration

Sources & evidence

ORD record
ord-1cdca9b0108b469eb8fecd095c52da43
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

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