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

HRID 2396876Notes

Reaction equation

HRID 2396876 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-0efef8f5c3c74f5d89b7562938077ef7
Source dataset
uspto-grants-1996_02
Patent number
US05495012

Reaction notes

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