Thiazolidinedione → HCID 10449281, compound

HRID 1394167Notes

Reaction equation

HRID 1394167 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=O)[CH3:15])[CH:9]=1.[S:17]1[CH2:21][C:20](=[O:22])[NH:19][C:18]1=[O:23].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10](/[C:14](=[C:21]2/[C:20](=[O:22])[NH:19][C:18](=[O:23])[S:17]/2)/[CH3:15])[CH:9]=1

Participants

6

Reactant 4

HCID 5437ThiazolidinedioneHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 51285771-(2′-Chloro[1,1′-biphenyl]-3-yl)ethanone

Product 1

HCID 10449281HCID 10449281, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a solution of 1-(2′-chloro-1,1′-biphenyl-3-yl)ethanone (145 mg, 0.63 mmol) and 2,4-thiazolidinedione (67 mg, 0.57 mmol) in xylene (1.9 mL), sodium acetate (38 mg, 0.28 mmol) and acetic anhydride (53 μL, 0.57 mmol) were added and the solution was heated in a sealed tube for 16 h. It was then cooled to rt, partitioned between ethyl acetate and water, washed with saturated sodium bicarbonate, brine and dried over sodium sulfate. Finally filtered, concentrated and purified by chromatography. (hexanes:ethyl acetate; 4:1) to give the product as a solid.

Workup

  1. temperaturethe solution was heated in a sealed tube for 16 h
  2. custompartitioned between ethyl acetate and water
  3. washwashed with saturated sodium bicarbonate, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFinally filtered
  6. concentrationconcentrated
  7. custompurified by chromatography

Sources & evidence

ORD record
ord-ff387f2a558f4804b46f5614fe0bd310
Source dataset
uspto-grants-2008_03
Patent number
US07348348B2

Reaction notes

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