Water → 3-Furan-2-ylmethyl-2-thioxo-thiazolidin-4-one

HRID 842301Notes

Reaction equation

HRID 842301 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[S:8]1[CH2:14][C:12](=[O:13])[NH:11][C:9]1=[S:10].C([O-])(=O)C.[Na+].O>C(O)(=O)C>[CH2:6]([N:11]1[C:12](=[O:13])[CH2:14][S:8][C:9]1=[S:10])[C:2]1[O:1][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7362FurfuralHCID 517045Sodium AcetateHCID 1201546Rhodanine

Product 1

HCID 5573973-Furan-2-ylmethyl-2-thioxo-thiazolidin-4-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-furaldehyde (43 mL) in hot glacial acetic acid (340 mL) was added rhodanine (68.4 g) and sodium acetate (128.4 g). The solution was refluxed for 0.5 hour and poured into water (2.6 L). The precipitate was collected by filtration and washed with water (1.4 L), ethanol (500 mL), and diethyl ether (200 mL). Recrystallization from acetone gave furfuryl rhodanine (97.4 g). The structure of the product was confirmed by NMR.

Workup

  1. temperatureThe solution was refluxed for 0.5 hour
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water (1.4 L), ethanol (500 mL), and diethyl ether (200 mL)
  4. customRecrystallization from acetone

Sources & evidence

ORD record
ord-fd99fbb1ff8d4e48ba1812489cc703be
Source dataset
uspto-grants-2002_04
Patent number
US06372895B1

Reaction notes

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