Hydrochloric Acid → 5-[4-(2-Oxoethoxy)benzyl]thiazolidine-2,4-dione

HRID 2294301Notes

Reaction equation

HRID 2294301 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([CH2:11][CH:12]2[S:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])=[CH:9][CH:8]=1)C.Cl>O1CCCC1>[O:3]=[CH:4][CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([CH2:11][CH:12]2[S:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23298348HCID 23298348, compound

Product 1

HCID 108492775-[4-(2-Oxoethoxy)benzyl]thiazolidine-2,4-dioneYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.07 g of 5-[4-(2,2-diethoxyethoxy)benzyl]-thiazolidine-2,4-dione (prepared as described in Preparation 19) were dissolved in 80 ml of tetrahydrofuran, and then 20 ml of 6N aqueous hydrochloric acid were added to the resulting solution. The mixture was then left to stand at room temperature overnight. At the end of this time, the solvent was removed from the reaction mixture by evaporation under reduced pressure, and water was added to the resulting residue, which was then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The ethyl acetate was removed from the extract by evaporation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a 3:2 by volume mixture of ethyl acetate and hexane as the eluent, to give 5.92 g of the title compound having an Rf value of 0.37 (on silica gel thin layer chromatography, using a 2:1 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

  1. waitThe mixture was then left
  2. customAt the end of this time, the solvent was removed from the reaction mixture by evaporation under reduced pressure, and water
  3. additionwas added to the resulting residue, which
  4. extractionwas then extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. customThe ethyl acetate was removed from the
  7. extractionextract by evaporation under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography
  9. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-75d12ea5ac8d4c35a444d941b1dc7359
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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