Thiazolidinedione → HCID 131725199, compound

HRID 1062467Notes

Reaction equation

HRID 1062467 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:19])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH: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.[NH2+]1CCCCC1>C1(C)C=CC=CC=1.N1CCCCC1.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:19])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[CH:5]=[C:24]1[S:20][C:21](=[O:26])[NH:22][C:23]1=[O:25]

Participants

7

Reactant 3

HCID 5437ThiazolidinedioneHCID 3014295Piperidinium acetateHCID 22277850HCID 22277850, compound

Product 1

HCID 131725199HCID 131725199, compoundYield 40.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 1140TolueneSolvent

Procedure

To a solution of the title compound of Step B (284 mg, 0.96 mmol) in toluene (16 ml) was added 2,4-thiazolidinedione (140 mg, 1.2 mmol), a catalytic amount of piperidinium acetate which was generated from piperidine (five drops) and acetic acid (five drops) and 4 Å molecular sieves. The mixture was stirred under reflux for about four hours, cooled to room temperature, filtered and concentrated. The product was purified by preparative TLC (4% methanol in dichloromethane) to afford the title compound (153 mg). MS (APCI−) Calc: 395.0, Found: 394.0 (M−1).

Workup

  1. temperatureunder reflux for about four hours
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe product was purified by preparative TLC (4% methanol in dichloromethane)

Sources & evidence

ORD record
ord-6b5aa9c73b1a404b84573df040ec3293
Source dataset
uspto-grants-2005_11
Patent number
US06960604B2

Reaction notes

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