Isopropanol → Isopropyl 4-Methyl-2-thioxopyrrolidine-3-carboxylate

HRID 2372373Notes

Reaction equation

HRID 2372373 reaction equation
[CH3:1][CH:2]1[CH2:6][NH:5][C:4](=[S:7])[CH:3]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH:13](O)(C)C>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[CH3:1][CH:2]1[CH2:6][NH:5][C:4](=[S:7])[CH:3]1[C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 19903350HCID 19903350, compound

Product 1

HCID 10465433Isopropyl 4-Methyl-2-thioxopyrrolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

To 5.0 g of ethyl 4-methyl-2-thioxopyrrolidine-3-carboxylate were added 300 ml of isopropyl alcohol and 11.4 g of titanium tetraisopropoxide. The resulting mixture was heated under reflux for 24 hours. After distilling off the excessive isopropyl alcohol under reduced pressure, water and chloroform were added to the residue and insoluble matters were filtered off. The chloroform layer was washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After distilling off the chloroform, 5.0 g of the title compound was obtained.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 24 hours
  3. distillationAfter distilling off the excessive isopropyl alcohol under reduced pressure, water and chloroform
  4. additionwere added to the residue and insoluble matters
  5. filtrationwere filtered off
  6. washThe chloroform layer was washed with water
  7. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate
  8. distillationAfter distilling off the chloroform

Sources & evidence

ORD record
ord-208e9c7149de4b728082e7eef87488b6
Source dataset
uspto-grants-1992_03
Patent number
US05098919

Reaction notes

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