Thionyl Chloride → HCID 10331021, compound

HRID 1885624Notes

Reaction equation

HRID 1885624 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[CH2:12][CH:11]([C:15](O)=[O:16])[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2].S(Cl)(Cl)=O>C(Cl)(Cl)(Cl)Cl>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:10][CH:11]([CH2:15][OH:16])[CH2:12][C:13]2=[O:14])=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 29006021-(4-ETHYLPHENYL)-2-OXOPYRROLIDINE-4-CARBOXYLIC ACID

Product 1

HCID 10331021HCID 10331021, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

1-(4-Ethylphenyl)-5-oxo-3-pyrrolidinecarboxylic acid (5.00 g) is suspended in carbon tetrachloride (15 ml) and thereto is added thionyl chloride (2.32 ml). The reaction mixture is heated with stirring under refluxing for 1 hour and concentrated under reduced pressure. The residue is dissolved in tetrahydrofuran (25 ml) and thereto is added dropwise a solution of sodium boron hydride (1.61 g) in dimethylformamide (about 16 ml) under ice-cooling. The mixture is further stirred for 1 hour. Methanol (13 ml) and conc. hydrochloric acid (1.87 ml) are successively added dropwise into the reaction mixture and the mixture is concentrated under reduced pressure. Ethyl acetate (120 ml) is added to the residue and the mixture is washed with water three times, dried over anhydrous magnesium sulfate, and then concentrated again under reduced pressure. To this residue is added a mixed solvent (about 50 ml) of ethyl acetate/hexane [1:20 (v/v)]. The mixture is allowed to stand and the precipitated crystal is collected by filtration to give the desired product (3.81 g).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder refluxing for 1 hour
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue is dissolved in tetrahydrofuran (25 ml)
  5. additionis added dropwise a solution of sodium boron hydride (1.61 g) in dimethylformamide (about 16 ml) under ice-
  6. temperaturecooling
  7. stirringThe mixture is further stirred for 1 hour
  8. additionMethanol (13 ml) and conc. hydrochloric acid (1.87 ml) are successively added dropwise into the reaction mixture
  9. concentrationthe mixture is concentrated under reduced pressure
  10. additionEthyl acetate (120 ml) is added to the residue
  11. washthe mixture is washed with water three times
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated again under reduced pressure
  14. additionTo this residue is added a mixed solvent (about 50 ml) of ethyl acetate/hexane [1:20 (v/v)]
  15. filtrationthe precipitated crystal is collected by filtration

Sources & evidence

ORD record
ord-8f29b34d3b1b486db652e4bf5487af44
Source dataset
uspto-grants-1992_09
Patent number
US05145865

Reaction notes

Loading…