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

HRID 862013Notes

Reaction equation

HRID 862013 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-43c390559a55407bac2b2581af2f2621
Source dataset
uspto-grants-1998_02
Patent number
US05716975

Reaction notes

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