5-((4-Hydroxyphenyl)methylene)-2,4-thiazolidinedione → 5-(4-Hydroxybenzyl)thiazolidine-2,4-dione

HRID 2217632Notes

Reaction equation

HRID 2217632 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([CH:6]=[C:7]2[S:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>C(O)(=O)C.[Pd]>[OH:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[S:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 5178225-((4-Hydroxyphenyl)methylene)-2,4-thiazolidinedioneHCID 2723923Ammonium formate

Product 1

HCID 101983975-(4-Hydroxybenzyl)thiazolidine-2,4-dioneYield 88.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a suspension of 51 (6.00 g, 27 mmol) in glacial acetic acid (100 mL) was added ammonium formate (6.27 g, 100 mmol) and 10% Pd on carbon (5.80 g) and the mixture was heated to vigorous reflux for 16 h. The mixture was cooled to room temperature then filtered through Celite. Most of the acetic acid was removed in vacuo then the crude product was dissolved in ethyl acetate (250 mL), washed with water (2×250 mL) then brine (250 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to yield a beige solid (5.35 g, 85%). 1H NMR: (400 MHz, DMSO-d6): δ 11.98 (bs, 1H), 9.32 (s, 1H), 7.02 (d, J=8.4 Hz, 2H), 6.68 (d, J=8.4 Hz, 2H), 4.82 (dd, J=8.4 and 4.0 Hz, 1H), 3.25 (dd, J=14.4 and 4.4 Hz, 1H), 2.99 (dd, J=14.0 and 9.2 Hz, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto vigorous reflux for 16 h
  3. filtrationthen filtered through Celite
  4. customMost of the acetic acid was removed in vacuo
  5. dissolutionthe crude product was dissolved in ethyl acetate (250 mL)
  6. washwashed with water (2×250 mL)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2cfb96ef7b5b4dea83ef6447bbeeb4e5
Source dataset
uspto-grants-2008_08
Patent number
US07407978B2

Reaction notes

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