Thiazolidinedione → HCID 73291302, compound

HRID 910052Notes

Reaction equation

HRID 910052 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[CH:14]=O)[CH3:2].[S:17]1[CH2:21][C:20](=[O:22])[NH:19][C:18]1=[O:23].C([O-])(=O)C.[NH4+]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[CH:14]=[C:21]1[S:17][C:18](=[O:23])[NH:19][C:20]1=[O:22])[CH3:2]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 517165Ammonium AcetateHCID 880259ethyl (4-bromo-2-formylphenoxy)acetate

Product 1

HCID 73291302HCID 73291302, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

4-Bromo-2-formylphenoxyacetic acid ethyl ester (2.47 g, 8.7 mmol), 2,4-thiazolidinedione (1.13 g (90%), 8.7 mmol), and ammonium acetate (671 mg, 8.7 mmol) was mixed with toluene (9 mL) in a sealed vial and heated by microwaves to 120° C. for 600 s. After cooling to room temperature and scratching the inside of the glass, the product precipitated out. The precipitate was filtered and washed with toluene to give the title compound as a yellow solid (2.38 g, 71%).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe product precipitated out
  3. filtrationThe precipitate was filtered
  4. washwashed with toluene

Sources & evidence

ORD record
ord-2440d957897c48e098b54333c81f22f0
Source dataset
uspto-grants-2011_09
Patent number
US08022063B2

Reaction notes

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