Thiazolidinedione → HCID 85132866, compound

HRID 2218966Notes

Reaction equation

HRID 2218966 reaction equation
[S:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].[OH:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[CH:12]=O.N1CCCCC1>C(O)C>[OH:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[CH:12]=[C:5]1[S:1][C:2](=[O:7])[NH:3][C:4]1=[O:6]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 697123-Hydroxy-4-nitrobenzaldehyde

Product 1

HCID 85132866HCID 85132866, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,4-thiazolidinedione (3.50 g, 30.0 mmol) in ethanol (120 mL) was added 3-hydroxy-4-nitrobenzaldehyde (5.00 g, 30.0 mmol) and piperidine (0.44 mL, 4.50 mmol). The mixture was stirred at reflux for 15 hours and then cooled to 0° C. The resulting precipitate was collected and washed with cold ethanol to afford 3.53 g of the desired compound as a brown solid. Further concentration and precipitation of the mother liquor afforded an additional 3.1 g of the product. This was used without further purification in the next reaction. 1H NMR (CDCl3)·8.20 (1H, d, J=8.8 Hz), 7.75 (1H, s), 7.26 (1H, s), 7.12 (1H, d, J=8.8 Hz).

Workup

  1. temperatureat reflux for 15 hours
  2. customThe resulting precipitate was collected
  3. washwashed with cold ethanol

Sources & evidence

ORD record
ord-02cab8cd6b154de2888300b8da58ee4b
Source dataset
uspto-grants-2008_08
Patent number
US07414040B2

Reaction notes

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