Toluene → HCID 86588863, compound

HRID 1790194Notes

Reaction equation

HRID 1790194 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].[CH3:42][N:43]1[C:47](=[O:48])[CH2:46][S:45][C:44]1=[O:49]>C(OCC)(=O)C.C(O)(=O)C>[CH3:42][N:43]1[C:47](=[O:48])[C:46](=[CH:28][C:27]2[CH:30]=[CH:31][C:32]([O:33][C:34]([F:37])([F:36])[F:35])=[C:25]([C:22]3[CH:23]=[C:24]4[C:19]([C:18]([CH3:39])([CH3:40])[CH2:17][C:16](=[O:41])[N:15]4[CH3:14])=[CH:20][C:21]=3[CH3:38])[CH:26]=2)[S:45][C:44]1=[O:49]

Participants

7

Reactant 4

HCID 1140TolueneHCID 8082PiperidineHCID 12820623-Methyl-1,3-thiazolidine-2,4-dioneHCID 21966438HCID 21966438, compound

Product 1

HCID 86588863HCID 86588863, compound

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 a 3-alkyl—thiazolidine-2,4-dione such as 3-Methyl-thiazolidine-2,4-dione (19.16 mmol) is heated at reflux overnight. The reaction mixture is cooled to room temperature, diluted with ethyl acetate and is washed with water and brine, dried over MgSO4. The residue is recrystallized to afford 3-methyl-5-[3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-4-trifluoromethoxy-benzylidene]-thiazolidine-2,4-dione.

Workup

  1. temperatureat reflux overnight
  2. washis washed with water and brine
  3. dry with materialdried over MgSO4
  4. customThe residue is recrystallized

Sources & evidence

ORD record
ord-5b00ee9768ad48a898dd923a0cb62874
Source dataset
uspto-grants-2006_07
Patent number
US07071218B2

Reaction notes

Loading…