Thiazolidinedione → HCID 74348953, compound

HRID 2382590Notes

Reaction equation

HRID 2382590 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:16][C:15]2[CH:17]=[C:18]([CH:21]=O)[CH:19]=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]1.[S:23]1[CH2:27][C:26](=[O:28])[NH:25][C:24]1=[O:29].C([O-])(=O)C.[NH2+]1CCCCC1>C1(C)C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:16][C:15]2[CH:17]=[C:18]([CH:21]=[C:27]3[S:23][C:24](=[O:29])[NH:25][C:26]3=[O:28])[CH:19]=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 3014295Piperidinium acetateHCID 86654536HCID 86654536, compound2×

Product 1

HCID 74348953HCID 74348953, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 4-benzooxazol-2-yl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepine-7-carbaldehyde [compound of Step VI] (0.176 g, 0.6 mmol) taken in toluene (25 mL) were added 2,4-thiazolidine dione (0.105 g, 0.9 mmol) and catalytic amount of piperidinium acetate (0.025 g). The resulting mixture was refluxed under Dean Stark conditions for 1.5 hours and then cooled in an ice-bath. The precipitate was filtered and washed with toluene and petroleum ether to give 5-(4-benzooxazol-2-yl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepin-7-ylmethylene)-thiazolidine-2,4-dione.

Workup

  1. temperatureThe resulting mixture was refluxed under Dean Stark conditions for 1.5 hours
  2. temperaturecooled in an ice-bath
  3. filtrationThe precipitate was filtered
  4. washwashed with toluene and petroleum ether

Sources & evidence

ORD record
ord-878ac6f22dea4cf88896500d4a61f3b8
Source dataset
uspto-grants-2012_09
Patent number
US08263587B2

Reaction notes

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