Water → 5-[[4-([1,1'-Biphenyl]-3-ylmethoxy)phenyl]methyl]-2,4-thiazolidinedione

HRID 2422222Notes

Reaction equation

HRID 2422222 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[S:13][C:12](=[O:14])[NH:11][C:10]2=[O:15])=[CH:4][CH:3]=1.Cl[CH2:17][C:18]1[CH:19]=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=[CH:22][CH:23]=1.[H-].[Na+].O>CS(C)=O>[C:20]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:21]=[CH:22][CH:23]=[C:18]([CH2:17][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH:9]3[S:13][C:12](=[O:14])[NH:11][C:10]3=[O:15])=[CH:6][CH:7]=2)[CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 101983975-(4-Hydroxybenzyl)thiazolidine-2,4-dioneHCID 154808923-(Chloromethyl)-1,1'-biphenyl

Product 1

HCID 859709065-[[4-([1,1'-Biphenyl]-3-ylmethoxy)phenyl]methyl]-2,4-thiazolidinedioneYield 256.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-[(4-hydroxyphenyl)methyl]-2,4-thiazolidinedione (0.30 g, 1.3 mmol) in dimethyl sulfoxide (20 mL) were added 3-(chloromethyl)biphenyl (0.26 g, 1.3 mmol) and 60% sodium hydride (0.11 g, 2.6 mmol), and the mixture was stirred at room temperature for 1 hr and further at 50° C. for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=8:2) to give the title compound (1.3 g, yield 96%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=8:2)

Sources & evidence

ORD record
ord-32202b138b64438db01d55fcb6f658b5
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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