Water → (+)-(4R)-4-acetylthiopyrrolidine-2-thione

HRID 21738Notes

Reaction equation

HRID 21738 reaction equation
C([C@H:4]1[CH2:8][NH:7][C:6](=[S:9])[CH2:5]1)(=O)C.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:11].O.[C:25]([O:28]CC)(=O)[CH3:26]>C1(C)C=CC=CC=1>[C:25]([S:11][C@H:4]1[CH2:8][NH:7][C:6](=[S:9])[CH2:5]1)(=[O:28])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14817Phosphorus sulfide (P2S5)HCID 86748733(4R)-4-acetylthio-2-pyrrolidone

Product 1

HCID 53742819(+)-(4R)-4-acetylthiopyrrolidine-2-thioneYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(4R)-4-Acetylthio-2-pyrrolidone (10 g) is dissolved in toluene (100 ml), and thereto is added gradually phosphorus pentasulfide (9.5 g), and the mixture is stirred at room temperature for 20 minutes. To the reaction solution are added water and ethyl acetate, and the mixture is stirred at room temperature for 1.5 hour. The insoluble materials are removed by filtration, and the organic layer is washed with water, dried, and evaporated to remove the solvent. The residue is recrystallized from toluene to give (+)-(4R)-4-acetylthiopyrrolidine-2-thione (7.9 g).

Workup

  1. stirringthe mixture is stirred at room temperature for 1.5 hour
  2. customThe insoluble materials are removed by filtration
  3. washthe organic layer is washed with water
  4. customdried
  5. customevaporated
  6. customto remove the solvent
  7. customThe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-c831e92724bb42c78a1ee0dcef2ad8e3
Source dataset
uspto-grants-1995_06
Patent number
US05424446

Reaction notes

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