Toluene → HCID 74062706, compound

HRID 1057858Notes

Reaction equation

HRID 1057858 reaction equation
C1(C)C=CC=CC=1.N1CCCCC1.[S:14]1[CH2:18][C:17](=[O:19])[NH:16][C:15]1=[O:20].[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][C:23]=1[C:30]1[C:39]([CH3:40])=[CH:38][C:37]2[C:36]([CH3:42])([CH3:41])[CH2:35][CH2:34][C:33]([CH3:44])([CH3:43])[C:32]=2[CH:31]=1>O.C(O)(=O)C>[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[C:18]2[S:14][C:15](=[O:20])[NH:16][C:17]2=[O:19])=[CH:24][C:23]=1[C:30]1[C:39]([CH3:40])=[CH:38][C:37]2[C:36]([CH3:42])([CH3:41])[CH2:35][CH2:34][C:33]([CH3:44])([CH3:43])[C:32]=2[CH:31]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 22268347HCID 22268347, compound

Product 1

HCID 74062706HCID 74062706, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of toluene (30 mL) containing piperidine (0.26 mL, 2.64 mmol) and acetic acid (0.26 mL) were added 2,4-thiazolidinedione (1.03 g, 8.81 mmol) and 4-chloro-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphtalen-2-yl)benzaldehyde (3.0 g, 8.81 mmol). The reaction mixture was heated at reflux for 12 hours with continuous removal of water using a Dean-Stark water separator. After cooling to room temperature, a yellow solid formed that was collected and washed with ethanol, dried under vacuum to give 2.7 g of 5-[4-chloro-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphtalen-2-yl)benzylidene]thiazolidine-2,4-dione (70% yield). 1H NMR (300 MHz; DMSO-d6): 1.19 (s, 3H); 1.20 (s, 3H); 1.25 (s, 3H); 1.26 (s, 3H); 1.63 (s, 4H); 2.01 (s, 3H); 7.07 (s, 1H); 7.26 (s, 1H); 7.52 (d, J=2.1 Hz, 1H); 7.59 (dd, J1=2.1 Hz, J2=8.1 Hz, 1H); 7.71 (d, J=8.1 Hz, 1H); 7.83 (s, 1H); 12.68 (s, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. customa yellow solid formed
  3. customthat was collected
  4. washwashed with ethanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-16a4bc6a36ff45f2b2d0b3fd91f58c49
Source dataset
uspto-grants-2003_02
Patent number
US06515003B1

Reaction notes

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