Water → HCID 57316763, compound

HRID 650580Notes

Reaction equation

HRID 650580 reaction equation
[CH3:1][C:2]1[C:3]([CH:16]([O:18][C:19]2[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=2)[CH3:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[S:27]1[CH2:31][C:30](=[O:32])[NH:29][C:28]1=[O:33].O>N1CCCCC1.C(O)(=O)C.C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:3]([CH:16]([O:18][C:19]2[CH:20]=[CH:21][C:22]([CH:23]=[C:31]3[S:27][C:28](=[O:33])[NH:29][C:30]3=[O:32])=[CH:25][CH:26]=2)[CH3:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

7

Reactant 3

HCID 962WaterHCID 5437ThiazolidinedioneHCID 21712645HCID 21712645, compound

Product 1

HCID 57316763HCID 57316763, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphtalene-2-yl)-ethoxy)-benzaldehyde (350 mg; 1.0 mmol), 2,4-thiazolidinedione (129 mg; 1.1 mmol), piperidine (1 drop) and acetic acid (1 drop) in toluene (10 ml) was refluxed for 3 hours using a water separator. Upon cooling to room temperature the product precipitated. Filtration gave the title compound in 325 mg (72%) yield.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customprecipitated
  3. filtrationFiltration

Sources & evidence

ORD record
ord-7fbebacac4834939bd1fe8f297e0f2c1
Source dataset
uspto-grants-2001_08
Patent number
US06274608B1

Reaction notes

Loading…