Acetic Acid → 4-Thiazolidinone, 5-[(4-phenoxyphenyl)methylene]-2-thioxo-

HRID 2258499Notes

Reaction equation

HRID 2258499 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:16]1[CH2:22][C:20](=[O:21])[NH:19][C:17]1=[S:18].C([O-])(=O)C.[Na+].C(O)(=O)C>O>[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[C:22]2[S:16][C:17](=[S:18])[NH:19][C:20]2=[O:21])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 661394-PhenoxybenzaldehydeHCID 517045Sodium AcetateHCID 1201546Rhodanine

Product 1

HCID 40886884-Thiazolidinone, 5-[(4-phenoxyphenyl)methylene]-2-thioxo-Yield 54.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9.9 g (50.0 mmol) of 4-phenoxybenzaldehyde, 6.8 g (51.1 mmol) of rhodanine, 15.5 g of sodium acetate and 60 ml of acetic acid was heated on a steam bath for two hours. The reaction solution was then poured into water causing crude product to precipitate. The precipitate was filtered and then washed successively with water followed by diethyl ether to provide 8.6 g of title product, m.p. 195°-200° C.

Workup

  1. temperaturewas heated on a steam bath for two hours
  2. customto precipitate
  3. filtrationThe precipitate was filtered
  4. washwashed successively with water

Sources & evidence

ORD record
ord-a26d435314ba4add88eeec9083226415
Source dataset
uspto-grants-1997_08
Patent number
US05661168

Reaction notes

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