Toluene → 5-(4-[2-(4-Methylmercaptophenyl)ethoxy]benzylidene)thiazolidine-2,4-dione

HRID 1595534Notes

Reaction equation

HRID 1595534 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.[S:20]1[CH2:24][C:23](=[O:25])[NH:22][C:21]1=[O:26].C1(C)C=CC=CC=1>N1CCCCC1.C(O)(=O)C.O>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[C:24]3[S:20][C:21](=[O:26])[NH:22][C:23]3=[O:25])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 537815244-[2-(4-Methylmercaptophenyl)ethoxy]benzaldehyde

Product 1

HCID 544653635-(4-[2-(4-Methylmercaptophenyl)ethoxy]benzylidene)thiazolidine-2,4-dioneYield 80%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 962WaterSolvent

Procedure

1 g (3.7 mmole) 4-[2-(4-Methylmercaptophenyl)ethoxy]benzaldehyde, 1.09 (9.25 mmole) 2,4-thiazolidinedione, 5 drops of piperidine, 6 drops of acetic acid and toluene were refluxed with water separation in a Dean-Stark apparatus for 1 hour. The heat was removed and the crystals were recrystallized in dichloromethane:methanol (95:5) to give 1.1 g (yield 80%) of 5-(4-[2-(4-methylmercaptophenyl)ethoxy]benzylidene)thiazolidine-2,4-dione.

Workup

  1. customThe heat was removed
  2. customthe crystals were recrystallized in dichloromethane:methanol (95:5)

Sources & evidence

ORD record
ord-6d70fe5c8ee4477abf8f8039d89eaad7
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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