Benzoic Acid → HCID 53707664, compound

HRID 427280Notes

Reaction equation

HRID 427280 reaction equation
[CH2:1]([O:3][CH:4]([O:15][CH2:16][CH3:17])[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)[CH3:2].[S:18]1[CH2:22][C:21](=[O:23])[NH:20][C:19]1=[O:24].C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1.CCOC(C)=O.O>[CH2:1]([O:3][CH:4]([O:15][CH2:16][CH3:17])[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[C:22]2[S:18][C:19](=[O:24])[NH:20][C:21]2=[O:23])=[CH:9][CH:8]=1)[CH3:2]

Participants

8

Reactant 4

HCID 243Benzoic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 187608894-(2,2-Diethoxyethoxy)benzaldehyde

Product 1

HCID 53707664HCID 53707664, compoundYield 83.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[(2,2-diethoxy]ethoxy]benzaldehyde (10.6 g, 44.53 mmol), thiazolidin-2,4-dione (5.21 g, 44.53 mmol), benzoic acid (0.70 g, 5.78 mmol) and piperidine (0.64 mL, 6.7 mmol) in toluene (150 mL) was refluxed for 2 h with continuous removal of water. The reaction mixture was cooled to room temperature and diluted with EtOAc (150 ml). The mixture was washed with water, brine, dried over anhydrous Na2SO4 and concentrated. The crude compound was purified by column chromatography using EtOAc:pet. ether (1:2) as eluent to afford the title compound (12.54 g, 70%) as a brown coloured liquid.

Workup

  1. washThe mixture was washed with water, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe crude compound was purified by column chromatography

Sources & evidence

ORD record
ord-08dba9a98b3e4661a8399b6bf0ae5527
Source dataset
uspto-grants-2001_11
Patent number
US06313113B1

Reaction notes

Loading…