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

HRID 1601820Notes

Reaction equation

HRID 1601820 reaction equation
Cl.C([O:4][CH:5](OCC)[CH2:6][O:7][C:8]1[CH:21]=[CH:20][C:11]([CH2:12][CH:13]2[S:17][C:16](=[O:18])[NH:15][C:14]2=[O:19])=[CH:10][CH:9]=1)C>O1CCCC1>[O:4]=[CH:5][CH2:6][O:7][C:8]1[CH:21]=[CH:20][C:11]([CH2:12][CH:13]2[S:17][C:16](=[O:18])[NH:15][C:14]2=[O:19])=[CH:10][CH:9]=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

20 ml of 6 N aqueous hydrochloric acid were added to a solution of 10.07 g of 5-[4-(2,2-diethoxyethoxy)benzyl]thiazolidine-2,4-dione (prepared as described in Preparation 46) in 80 ml of tetrahydrofuran, and the resulting mixture was allowed to stand overnight at room temperature. At the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure. The residue was diluted with water, after which it was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 2:3 by volume mixture of hexane and ethyl acetate as the eluent, to give 5.92 g of the title compound having Rf=0.37 (on silica gel thin layer chromatography using a 1:2 by volume mixture of hexane and ethyl acetate as the developing solvent).

Workup

  1. distillationAt the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionafter which it was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe resulting residue was purified by column chromatography through silica gel
  7. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-24d6d2971ed04456a419bc3bc7759cce
Source dataset
uspto-grants-1999_11
Patent number
US05977365

Reaction notes

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