Thiazolidinedione → HCID 85051391, compound

HRID 488844Notes

Reaction equation

HRID 488844 reaction equation
N1CCCCC1.[S:7]1[CH2:11][C:10](=[O:12])[NH:9][C:8]1=[O:13].[F:14][C:15]([F:41])([F:40])[O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][C:18]=1[C:25]1[C:34]([CH3:35])=[CH:33][C:32]2[C:31]([CH3:37])([CH3:36])[CH2:30][CH2:29][C:28]([CH3:39])([CH3:38])[C:27]=2[CH:26]=1>C1(C)C=CC=CC=1.O.C(O)(=O)C>[CH3:35][C:34]1[C:25]([C:18]2[CH:19]=[C:20]([CH:23]=[CH:24][C:17]=2[O:16][C:15]([F:14])([F:41])[F:40])[CH:21]=[C:11]2[S:7][C:8](=[O:13])[NH:9][C:10]2=[O:12])=[CH:26][C:27]2[C:28]([CH3:39])([CH3:38])[CH2:29][CH2:30][C:31]([CH3:36])([CH3:37])[C:32]=2[CH:33]=1

Participants

7

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 22041392HCID 22041392, compound

Product 1

HCID 85051391HCID 85051391, compoundYield 47.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Procedure

To a solution of toluene (50 mL) containing piperidine (0.84 mL, 8.53 mmol) and acetic acid (0.84 mL) was added 2,4-thiazolidinedione (3.3 g, 28.43 mmol) and 4-trifluoromethoxy-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)benzaldehyde (11.1 g, 28.43 mmol). The reaction mixture was heated at reflux with continuous removal of water using a Dean-Stark water separator. After 12 hours at reflux 25 mL of toluene was removed by distillation and the solution was cooled to room temperature. The yellow solid was collected and taken up in ethanol (40 ml). After stirring at room temperature for 15 minutes, the pale yellow solid was collected and washed with a minimum of ethanol, dried under vacuum to give 6.6 g of 3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-trifluoromethoxybenzylidene-2,4-thiazolidinedione. The organic layers were combined and evaporated. Further crystallization from ethanol afforded an additional 2.0 g to give a total of 8.6 g (61%) of product. 1H NMR (300 MHz; DMSO-d6): 1.21 (s, 6H); 1.27 (s, 6H); 1.65 (s, 4H); 2.04 (s, 3H); 7.08 (s, 1H); 7.26 (s, 1H); 7.62 (m, 2H); 7.70 (dd, J1=8.0 Hz, J2=1.52 Hz, 1H); 7.86 (s, 1H); 12.5 (s, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. customwas removed by distillation
  3. customThe yellow solid was collected
  4. customthe pale yellow solid was collected
  5. washwashed with a minimum of ethanol
  6. customdried under vacuum

Sources & evidence

ORD record
ord-03de6e14f86a40799fbbe5ca88629744
Source dataset
uspto-grants-2005_12
Patent number
US06974826B2

Reaction notes

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