Benzaldehyde → 5-Benzylidene-2,4-thiazolidinedione

HRID 1729052Notes

Reaction equation

HRID 1729052 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:9]1[CH2:13][C:12](=[O:14])[NH:11][C:10]1=[O:15]>N1C=CC=CC=1.CN(C)C=O.CCCCCC.O>[C:2]1([CH:1]=[C:13]2[S:9][C:10](=[O:15])[NH:11][C:12]2=[O:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 240BenzaldehydeHCID 5437Thiazolidinedione

Product 1

HCID 1991545-Benzylidene-2,4-thiazolidinedioneYield 109.3%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
55 °C

Procedure

Benzaldehyde (0.78 mol, 82.8 g) and 2,4-thiazolidinedione (0.85 mol, 100 g)were heated to reflux in a mixture of pyridine (215 mL) and dimethylformamide (400 ml) for 18 hours. The reaction mixture was cooled to 55° C., diluted with hexane (360 mL) and water (900 mL), and stirred for 1 hour after cooling to room temperature. The product was collected to afford 175 g of title product as a pale yellow solid; mp 246°-248° C.

Workup

  1. temperatureafter cooling to room temperature
  2. customThe product was collected

Sources & evidence

ORD record
ord-eeccde95adaf483681b4a76aa093576b
Source dataset
uspto-grants-1994_07
Patent number
US05330998

Reaction notes

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