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

HRID 259766Notes

Reaction equation

HRID 259766 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-466c9ca65b424ce2841a4213aea2c06e
Source dataset
uspto-grants-1996_06
Patent number
US05523314

Reaction notes

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