Toluene → HCID 86590247, compound

HRID 2212578Notes

Reaction equation

HRID 2212578 reaction equation
C1(C)C=CC=CC=1.N1CCCCC1.[CH3:14][N:15]1[C:24]2[C:19](=[CH:20][C:21]([CH3:38])=[C:22]([C:25]3[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=3[O:33][C:34]([F:37])([F:36])[F:35])[CH:28]=O)[CH:23]=2)[C:18]([CH3:40])([CH3:39])[CH2:17][C:16]1=[O:41].[S:42]1[CH2:46][C:45](=[O:47])[NH:44][C:43]1=[O:48]>C(OCC)(=O)C.C(O)(=O)C>[CH3:14][N:15]1[C:24]2[C:19](=[CH:20][C:21]([CH3:38])=[C:22]([C:25]3[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=3[O:33][C:34]([F:35])([F:37])[F:36])[CH:28]=[C:46]3[S:42][C:43](=[O:48])[NH:44][C:45]3=[O:47])[CH:23]=2)[C:18]([CH3:39])([CH3:40])[CH2:17][C:16]1=[O:41]

Participants

7

Reactant 4

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 21966438HCID 21966438, compound

Product 1

HCID 86590247HCID 86590247, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of toluene (80 mL), piperidine (380 μL), acetic acid (380 μL), 3-(1,4,4,6-Tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-4-trifluoromethoxy-benzaldehyde (7.5 g, 19.16 mmol) and 2,4-thiazolidinedione (2.25 g, 19.16 mmol) was heated at reflux overnight. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with water and brine, dried over MgSO4. The residue was recrystallized successively from ethanol, dichloromethane/hexane and ethanol to afford 4.3 g (46%) of 5-[3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-4-trifluoromethoxy-benzylidene]-thiazolidine-2,4 dione. mp 182–184° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. customThe residue was recrystallized successively from ethanol, dichloromethane/hexane and ethanol

Sources & evidence

ORD record
ord-eed2d705dc59468faa6da20edeac562a
Source dataset
uspto-grants-2006_09
Patent number
US07102000B2

Reaction notes

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