Benzoyl chloride → 5-(4-Benzoylaminophenyl)thiazolidine-2,4-dione

HRID 1742824Notes

Reaction equation

HRID 1742824 reaction equation
O1CCOCC1.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[S:18][C:17](=[O:19])[NH:16][C:15]2=[O:20])=[CH:10][CH:9]=1.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(N(CC)CC)C>[C:21]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]2[S:18][C:17](=[O:19])[NH:16][C:15]2=[O:20])=[CH:12][CH:13]=1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 312751,4-DioxaneHCID 128509725-(4-Aminophenyl)thiazolidine-2,4-dione

Product 1

HCID 190060595-(4-Benzoylaminophenyl)thiazolidine-2,4-dioneYield 93.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Into 20 ml of dioxane were dissolved 0.5 g of 5-(4-aminophenyl) thiazolidine-2,4-dione, and, after added 0.34 g of benzoyl chloride and further added dropwise 0.24 g of triethylamine, the mixture was refluxed for 1 hour. After cooling by standing, the reaction mixture was poured into 150 ml of ice water and the crystals deposited were collected by filtration, washed with water and dried. These were recrystallized from chloroform to obtain 0.70 g of title compound.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureAfter cooling
  3. filtrationthe crystals deposited were collected by filtration
  4. washwashed with water
  5. customdried
  6. customThese were recrystallized from chloroform

Sources & evidence

ORD record
ord-9beb242176cd4c92aac25d7e1e4edc8e
Source dataset
uspto-grants-1994_08
Patent number
US05342850

Reaction notes

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