3-Thiazolidineacetic acid, 4-oxo-2-thioxo- → HCID 72394820, compound

HRID 2213577Notes

Reaction equation

HRID 2213577 reaction equation
[S:1]1[CH2:7][C:5](=[O:6])[N:4]([CH2:8][C:9]([OH:11])=[O:10])[C:2]1=[S:3].[C:12]1([CH:18]([O:23][C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=2[O:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:27]=O)[C:19]([F:22])([F:21])[F:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C.C(OCC)(=O)C>[C:12]1([CH:18]([O:23][C:24]2[CH:25]=[C:26]([CH:27]=[C:7]3[S:1][C:2](=[S:3])[N:4]([CH2:8][C:9]([OH:11])=[O:10])[C:5]3=[O:6])[CH:29]=[CH:30][C:31]=2[O:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:19]([F:22])([F:21])[F:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 797933-Thiazolidineacetic acid, 4-oxo-2-thioxo-HCID 517045Sodium AcetateHCID 21957443HCID 21957443, compound

Product 1

HCID 72394820HCID 72394820, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of rhodanine-3-acetic acid (87 mg, 0.46 mmol, 1 eq), 3-(1-phenyl-2,2,2-trifluoroethoxy)-4-(2-phenylethoxy)benzaldehyde (183 mg, 0.46 mmol, 1 eq) and sodium acetate (112 mg, 1.37 mmol, 3 eq) in acetic acid (2 mL) was heated to 150□C and stirred for 3.5 days. The reaction mixture was then cooled to room temperature and partitioned between ethyl acetate (50 mL) and water (50 mL) and the two layers separated. The organic layer was washed with 1M HCl (2×50 mL), and loaded onto silica. Elution with ethyl acetate:methanol (4:1) gave a yellow gum. This was dissolved in hot ethyl acetate and filtered (to remove some insoluble material). The filtrate was allowed to cool to room temperature and diethyl ether added. This gave a suspension which was again filtered. The filtrate was evaporated and the residue redissolved in diethyl ether. Addition of petroleum ether to the solution gave a precipitate which was filtered off. The mother liquor was evaporated and the resulting gum was crystallized from diethyl ether and petroleum ether to give the product as a yellow powder (107 mg, 41%) mp 170° C.: 1H NMR (d6 DMSO) δ 7.67 (s, 1H, C═C—H), 6.17 (q, 1H, J 6.5 Hz, CHCF3), 4.70 (s, 2H, CH2CO2H), 4.33 (t, 2H, J 5.9 Hz, OCH2CH2Ph), 3.09 (t, 2H, J 6.2 Hz, OCH2CH2Ph).

Workup

  1. custompartitioned between ethyl acetate (50 mL) and water (50 mL)
  2. customthe two layers separated
  3. washThe organic layer was washed with 1M HCl (2×50 mL)
  4. washElution with ethyl acetate:methanol (4:1)
  5. customgave a yellow gum
  6. filtrationfiltered (
  7. customto remove some insoluble material)
  8. temperatureto cool to room temperature
  9. additiondiethyl ether added
  10. customThis gave a suspension which
  11. filtrationwas again filtered
  12. customThe filtrate was evaporated
  13. dissolutionthe residue redissolved in diethyl ether
  14. additionAddition of petroleum ether to the solution
  15. customgave a precipitate which
  16. filtrationwas filtered off
  17. customThe mother liquor was evaporated
  18. customthe resulting gum was crystallized from diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-f891100b488d40e0b410b6e6f7347e48
Source dataset
uspto-grants-2006_09
Patent number
US07105554B2

Reaction notes

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