Toluene → HCID 74062707, compound

HRID 1765428Notes

Reaction equation

HRID 1765428 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].[CH3:21][N:22]([CH3:46])[C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][C:24]=1[C:31]1[C:40]([CH3:41])=[CH:39][C:38]2[C:37]([CH3:43])([CH3:42])[CH2:36][CH2:35][C:34]([CH3:45])([CH3:44])[C:33]=2[CH:32]=1>O.C(O)(=O)C>[CH3:46][N:22]([CH3:21])[C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[C:18]2[S:14][C:15](=[O:20])[NH:16][C:17]2=[O:19])=[CH:25][C:24]=1[C:31]1[C:40]([CH3:41])=[CH:39][C:38]2[C:37]([CH3:42])([CH3:43])[CH2:36][CH2:35][C:34]([CH3:45])([CH3:44])[C:33]=2[CH:32]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 22268360HCID 22268360, compound

Product 1

HCID 74062707HCID 74062707, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of toluene (30 mL) containing piperidine (0.2 mL) and acetic acid (0.2 mL) were added 2,4-thiazolidinedione (2.34 g, 20 mmol) and 4-dimethylamino-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphtalen-2-yl)benzaldehyde (7.0 g, 20 mmol). The reaction mixture was heated at reflux for 4 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 5.7 g of 5-[4-dimethylamino-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphtalen-2-yl)benzylidene]thiazolidine-2,4-dione. The organic layers were combined and evaporated. Trituration from ethanol afforded 1.4 g more of product (78%). 1H NMR (300 MHz; d-DMSO): 1.21 (s, 3H); 1.24 (s, 3H); 1.27 (s , 6H); 1.65 (s, 4H); 2.05 (s, 3H); 2.55 (s, 6H); 7.06 (d, J=9 Hz, 1H); 7.13 (s, 1H); 7.20 (s, 1H); 7.21 (d, J=2.4 Hz, 1H); 7.46 (dd, J1=2.1 Hz, J2=8.7 Hz, 1H); 7.73 (s, 1H); 12.43 (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-bcd146c866d9411aafdcc6e5388ae0ec
Source dataset
uspto-grants-2007_06
Patent number
US07226940B2

Reaction notes

Loading…