Thiazolidinedione → HCID 74348952, compound

HRID 2382583Notes

Reaction equation

HRID 2382583 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:13][C:12]2[CH:14]=[C:15]([CH:18]=O)[CH:16]=[CH:17][C:11]=2[O:10][CH2:9][CH2:8]1.[S:20]1[CH2:24][C:23](=[O:25])[NH:22][C:21]1=[O:26].C([O-])(=O)C.[NH2+]1CCCCC1>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:13][C:12]2[CH:14]=[C:15]([CH:18]=[C:24]3[S:20][C:21](=[O:26])[NH:22][C:23]3=[O:25])[CH:16]=[CH:17][C:11]=2[O:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 3014295Piperidinium acetateHCID 86654534HCID 86654534, compound

Product 1

HCID 74348952HCID 74348952, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Pyridin-2-yl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepine-7-carbaldehyde [compound of Example 1-Step III] (0.868 g, 3.4 mmol) was dissolved in 100 mL dry toluene and to this solution, was added 2,4-thiazolidinedione (0.402 g, 3.4 mmol) and piperidinium acetate (46 mg, 0.32 mmol). The reaction mixture was refluxed in a Dean Stark apparatus for 4 hours. The reaction mixture was cooled and filtered. The residue was washed with petroleum ether (500 mL) and dried in air to give crude material A (0.6 g). The filtrate and petroleum ether wash were combined, cooled overnight and filtered. The filtrate was washed with petroleum ether (500 mL). The residue was dried in air to give crude material B (0.24 g). Both crude materials, A and B were combined and purified by silica chromatography using 1% CH2Cl2 in MeOH to give 5-(4-pridin-2-yl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepin-7-ylmethylene)-thiazolidine-2,4-dione.

Workup

  1. temperatureThe reaction mixture was refluxed in a Dean Stark apparatus for 4 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. washThe residue was washed with petroleum ether (500 mL)
  5. customdried in air
  6. customto give crude material A (0.6 g)
  7. washThe filtrate and petroleum ether wash
  8. temperaturecooled overnight
  9. filtrationfiltered
  10. washThe filtrate was washed with petroleum ether (500 mL)
  11. customThe residue was dried in air
  12. customto give crude material B (0.24 g)
  13. custompurified by silica chromatography

Sources & evidence

ORD record
ord-75a2c8338cf944c8af425a7559dfcee2
Source dataset
uspto-grants-2012_09
Patent number
US08263587B2

Reaction notes

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