Ammonium Hydroxide → 5-(4-Quinolinylmethylene)-2-thioxo-4-thiazolidinone

HRID 2258497Notes

Reaction equation

HRID 2258497 reaction equation
[S:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[S:3].[OH-].[NH4+].[Cl-].[NH4+].[N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH:22]=O)=[CH:14][CH:13]=1>C(O)C>[N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH:22]=[C:7]2[S:1][C:2](=[S:3])[NH:4][C:5]2=[O:6])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 780724-QuinolinecarboxaldehydeHCID 1201546Rhodanine

Product 1

HCID 43702165-(4-Quinolinylmethylene)-2-thioxo-4-thiazolidinoneYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

Rhodanine (2.2 g; 16.5 mmol), 1.3 ml of concentrated ammonium hydroxide and 1 g of ammonium chloride in 20 ml of ethanol were heated on a steam bath for 15 minutes. 4-Quinoline carboxaldehyde (2.6 g; 16.5 mmol) was added and the resulting mixture was heated on the steam bath for another hour. Upon cooling to 5° C. a precipitate formed. This precipitate was recovered by filtration and then washed with water to provide 4 g of title compound, m.p. 325°-328° C.

Workup

  1. temperaturethe resulting mixture was heated on the steam bath for another hour
  2. customformed
  3. filtrationThis precipitate was recovered by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-5b56b6900c764ecdacbc3dcc1d85a4fc
Source dataset
uspto-grants-1997_08
Patent number
US05661168

Reaction notes

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