Thiazolidinedione → HCID 72085102, compound

HRID 1281133Notes

Reaction equation

HRID 1281133 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[S:5][CH:6]=1.[S:9]1[CH2:13][C:12](=[O:14])[NH:11][C:10]1=[O:15].N1CCCCC1>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:13]2[S:9][C:10](=[O:15])[NH:11][C:12]2=[O:14])[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 877924-Bromothiophene-2-carbaldehyde

Product 1

HCID 72085102HCID 72085102, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-bromothiophene-2-carboxaldehyde (1.91 g, 10.0 mmol) and 2,4-thiazolidinedione (1.40 g, 12.0 mmol) in ethanol (30 mL) was added piperidine (1.0 mL, 10.0 mmol). The reaction mixture was heated at reflux for 3 h, then cooled on an ice-bath, and the precipitated products were collected by filtration. The cake was washed with 40% ethanol and dried to afford 5-(4-bromothiophen-2-ylmethylene)-2,4-thiazolidinedione (2.53 g, 87%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. temperaturecooled on an ice-bath
  4. filtrationthe precipitated products were collected by filtration
  5. washThe cake was washed with 40% ethanol
  6. customdried

Sources & evidence

ORD record
ord-f1fa282738b840ddb40b25a4c4d9872a
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

Loading…