Thiazolidinedione → 3-[2-(4-Chlorophenyl)-2-oxoethyl]-1,3-thiazolidine-2,4-dione

HRID 889821Notes

Reaction equation

HRID 889821 reaction equation
[H-].[Na+].[S:3]1[CH2:7][C:6](=[O:8])[NH:5][C:4]1=[O:9].Br[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[O:13].C(OCC)(=O)C>CN(C=O)C.CCCCCC.O>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:12](=[O:13])[CH2:11][N:5]2[C:6](=[O:8])[CH2:7][S:3][C:4]2=[O:9])=[CH:15][CH:16]=1

Participants

8

Reactant 4

HCID 5437ThiazolidinedioneHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 68303p-Chlorophenacyl bromide

Product 1

HCID 12061653-[2-(4-Chlorophenyl)-2-oxoethyl]-1,3-thiazolidine-2,4-dioneYield 85%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

To a suspension of 3.15 g of sodium hydride (60% in mineral oil, 78.8 mmol) in 70 mL of DMF at 0° C. was added 9.76 g (75 mmol) of 2,4-thiazolidinedione portion-wise. The reaction mixture was stirred for 20 minutes, then 17.5 g of 2-bromo-4′-chloroacetophenone (75 mmol) was added. The reaction was allowed to warm to room temperature and stirred for 5 hours. Ethyl acetate and water were added, the organic phase was separated, and washed with water and brine. The combined aqueous extracts were washed with additional ethyl acetate which was then washed with water and brine and combined with the rest of the organic layer. The ethyl acetate phases were dried over magnesium sulfate, filtered and stripped to give 23 g of crude product. Recrystallization from 1:1 toluene:hexane gave 16.25 g of 3-(2-(4-chlorophenyl)-2-oxo-ethyl)-thiazolidine-2,4-dione, (85% yield) mp 122–124° C.

Workup

  1. stirringstirred for 5 hours
  2. customthe organic phase was separated
  3. washwashed with water and brine
  4. washThe combined aqueous extracts were washed with additional ethyl acetate which
  5. washwas then washed with water and brine
  6. dry with materialThe ethyl acetate phases were dried over magnesium sulfate
  7. filtrationfiltered
  8. customto give 23 g of crude product
  9. customRecrystallization from 1:1 toluene

Sources & evidence

ORD record
ord-e81f4e004d61406bbb5baa4caf1f3484
Source dataset
uspto-grants-2006_02
Patent number
US06995157B2

Reaction notes

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