4-Toluenesulfonyl chloride → 5-(4-(p-Toluenesulfonylamino)phenyl)thiazolidine-2,4-dione

HRID 1742826Notes

Reaction equation

HRID 1742826 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[S:12][C:11](=[O:13])[NH:10][C:9]2=[O:14])=[CH:4][CH:3]=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH:8]3[S:12][C:11](=[O:13])[NH:10][C:9]3=[O:14])=[CH:6][CH:7]=2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 128509725-(4-Aminophenyl)thiazolidine-2,4-dione

Product 1

HCID 190060605-(4-(p-Toluenesulfonylamino)phenyl)thiazolidine-2,4-dioneYield 74.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into 10 ml of pyridine were dissolved 0.50 g of 5-(4-amino-phenyl) thiazolidine-2,4-dione, and after added 0.46 g of p-toluenesulfonyl chloride, the mixture was stirred for 1 hour at room temperature. After the completion of reaction, the reaction mixture was poured into ice water, which was extracted with ethyl acetate. The organic layer was washed with 10% hydrochloric acid, washed with water and dried. Then, solvent was distilled off. The residue was recrystallized from benzene to obtain 0.65 g of title compound.

Workup

  1. customAfter the completion of reaction
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with 10% hydrochloric acid
  4. washwashed with water
  5. customdried
  6. distillationThen, solvent was distilled off
  7. customThe residue was recrystallized from benzene

Sources & evidence

ORD record
ord-a9d060056e9d435e97a88f6f23bac97d
Source dataset
uspto-grants-1994_08
Patent number
US05342850

Reaction notes

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