Hydrochloric Acid → 5-(4-Piperonyloylaminophenyl)thiazolidine-2,4-dione

HRID 1742825Notes

Reaction equation

HRID 1742825 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](O)(=[O:25])[C:16]1[CH:24]=[CH:23][C:22]2[O:21][CH2:20][O:19][C:18]=2[CH:17]=1.C(P(C#N)(CC)=O)C.Cl>O.C(N(CC)CC)C.CN(C)C=O>[C:15]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[S:12][C:11](=[O:13])[NH:10][C:9]2=[O:14])=[CH:6][CH:7]=1)(=[O:25])[C:16]1[CH:24]=[CH:23][C:22]2[O:21][CH2:20][O:19][C:18]=2[CH:17]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 71961,3-Benzodioxole-5-carboxylic acidHCID 128509725-(4-Aminophenyl)thiazolidine-2,4-dioneHCID 13586794Diethylphosphorylcyanide

Product 1

HCID 190060615-(4-Piperonyloylaminophenyl)thiazolidine-2,4-dioneYield 61.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Into 20 ml of dimethylformamide were dissolved 1.00 g of 5-(4-aminophenyl)thiazolidine-2,4-dione and 0.80 g of piperonylic acid, and, after added 1.12 g of diethylphosphoryl cyanide and then 0.50 g of triethylamine at 0° C., the mixture was stirred for 1 hour as it was. Thereafter, the reaction mixture was brought to room temperature and stirred for 2 hours. Then, it was poured into 200 ml of water and, after made acidic with hydrochloric acid, the crystals deposited were collected by filtration. These were recrystallized from ethanol to obtain 1.05 g of title compound.

Workup

  1. customwas brought to room temperature
  2. filtrationthe crystals deposited were collected by filtration
  3. customThese were recrystallized from ethanol

Sources & evidence

ORD record
ord-0626c4fc921d4926a5a83c6bd146ce74
Source dataset
uspto-grants-1994_08
Patent number
US05342850

Reaction notes

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