Stannous Chloride → (Z)-3-(4-aminobenzyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

HRID 517609Notes

Reaction equation

HRID 517609 reaction equation
[CH2:1]([O:3][C:4]1[CH:27]=[CH:26][C:7](/[CH:8]=[C:9]2/[C:10](=[O:25])[N:11]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[C:12](=[O:14])[S:13]/2)=[CH:6][CH:5]=1)[CH3:2].[Sn](Cl)Cl>C(Cl)(Cl)Cl.C(O)C.ClCCl>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:11]2[C:10](=[O:25])/[C:9](=[CH:8]/[C:7]3[CH:26]=[CH:27][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=3)/[S:13][C:12]2=[O:14])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 1498888(Z)-5-(4-ethoxybenzylidene)-3-(4-nitrobenzyl)thiazolidine-2,4-dione

Product 1

HCID 71697762(Z)-3-(4-aminobenzyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21889567Chloroform ethanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of compound 28n (100 mg, 0.26 mol) in 10 mL of chloroform-ethanol co-solvent (ratio, 4:1) was added tin(II) chloride.dihydrate (293 mg, 1.30 mmol). The reaction mixture was stirred at 45° C. overnight. The reaction mixture was diluted with dichloromethane and washed with sat'd aqueous NaHCO3, collected the organic layer, dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography (10% ethyl acetate in dichloromethane) to afford 88 mg (97.0%) of pure 28o as a yellow-orange solid.

Workup

  1. washwashed with sat'd aqueous NaHCO3
  2. customcollected the organic layer
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica column chromatography (10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-38df7d3e6da349e6860c626c4f6cafc0
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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