Thiazolidinedione → HCID 58312726, compound

HRID 1397005Notes

Reaction equation

HRID 1397005 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([CH:9]=O)[CH:6]=[CH:5][N:4]=1.[S:11]1[CH2:15][C:14](=[O:16])[NH:13][C:12]1=[O:17].N1CCCCC1>C(O)C>[CH3:1][S:2][C:3]1[N:8]=[C:7](/[CH:9]=[C:15]2/[C:14](=[O:16])[NH:13][C:12](=[O:17])[S:11]/2)[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 154070082-Methylsulfanylpyrimidine-4-carbaldehyde

Product 1

HCID 58312726HCID 58312726, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A 40 mL round-bottomed vial was charged with 2-(methylthio)pyrimidine-4-carbaldehyde (4) (771 mg, 5 mmol), thiazolidine-2,4-dione (586 mg, 5 mmol, 1.0 equiv.), and piperidine (400 μL, 4 mmol, 0.8 equiv.) in ethanol (20 mL, 0.25 M). The reaction mixture was heated to 80° C. and shaken for 20 h. The resulting yellow precipitate was isolated by filtration and washed with ethanol (1×20 mL) and dried in vacuo to afford (Z)-5-((2-(methylthio)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione (5) as a yellow solid (550 mg, 898 mg theoretical, 61%). LC-MS m/z 254 (M+1).

Workup

  1. customThe resulting yellow precipitate was isolated by filtration
  2. washwashed with ethanol (1×20 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-954fe9e15c914244a50e5530ce5d0479
Source dataset
uspto-grants-2014_12
Patent number
US08901145B2

Reaction notes

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