Water → HCID 13662502, compound

HRID 652238Notes

Reaction equation

HRID 652238 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:13](=[O:14])[CH2:12][CH2:11][CH:10]2[C:15]([OH:17])=O)[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:15](=[O:17])[CH:10]3[CH2:11][CH2:12][C:13](=[O:14])[N:9]3[CH2:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 4379030HCID 4379030, compoundHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13662502HCID 13662502, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 25.37 g of (±)-1-[(3-chlorophenyl)methyl]-5-oxo-2-pyrrolidinecarboxylic acid in sieve dried dichloromethane (20 ml), 13.09 g of thionyl chloride was added, and the resultant solution was stirred and refluxed with the exclusion of moisture for 6 hours. An infrared spectrum of the solution indicated the presence of the acid chloride. After standing overnight at ambient temperature, the solution was chilled to 5° C. and 40 g of aluminum chloride was added in portions with exclusion of moisture and vigorous stirring. The reaction was slightly exothermic and a solid began to precipitate. The flask was heated intermittently with a steam bath to increase the rate of the reaction. After each heating, the gas evolution was allowed to subside. When heating did not produce gas evolution, ice chips were added to quench the reaction. Water was then added to the mixture and the phases were separated. The aqueous phase was extracted with dichloromethane and the combined organic phase was dried (Na2SO4). The mixture was vacuum filtered and concentrated to a solid to which ethyl acetate was added and the resultant mixture was vacuum filtered to give 11.56 g of a solid. The solid was dried overnight under vacuum.

Workup

  1. temperaturerefluxed with the exclusion of moisture for 6 hours
  2. customto precipitate
  3. temperatureThe flask was heated intermittently with a steam bath
  4. temperatureto increase
  5. customthe rate of the reaction
  6. temperatureWhen heating
  7. customdid not produce gas evolution, ice chips
  8. additionwere added
  9. customto quench
  10. customthe reaction
  11. customthe phases were separated
  12. extractionThe aqueous phase was extracted with dichloromethane
  13. dry with materialthe combined organic phase was dried (Na2SO4)
  14. filtrationfiltered
  15. concentrationconcentrated to a solid to which ethyl acetate
  16. additionwas added
  17. filtrationfiltered

Sources & evidence

ORD record
ord-911582338ff54a94a504c61ec2d36962
Source dataset
uspto-grants-1987_06
Patent number
US04670562

Reaction notes

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