Thiazolidinedione → HCID 86616530, compound

HRID 1932443Notes

Reaction equation

HRID 1932443 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=1)[CH:5]=O.[S:20]1[CH2:24][C:23](=[O:25])[NH:22][C:21]1=[O:26].C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=1)[CH:5]=[C:24]1[S:20][C:21](=[O:26])[NH:22][C:23]1=[O:25]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 9793820Piperidine, acetateHCID 86616531HCID 86616531, compound

Product 1

HCID 86616530HCID 86616530, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-methyl-4-(5-nitropyridin-2-yloxy)benzaldehyde (600 mg, 2.32 mmol) in toluene (35 mL) were added 2,4-thiazolidinedione (270 mg, 2.31 mmol) and piperidine acetate (135 mg, 0.93 mmol). The resulting solution was attached to a Dean Stark, and stirred under reflux for 1.5 hours. After being left to cool for 17 hours at room temperature, the precipitated yellow powder was filtered, to thereby yield 600 mg of the title compound.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. waitAfter being left
  3. filtrationthe precipitated yellow powder was filtered

Sources & evidence

ORD record
ord-617fbcaffb93427682f285269b621ead
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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