Water → 4-Thiazolidinone,5-[(5-methyl-2-furanyl)methylene]-2-thioxo-

HRID 1900100Notes

Reaction equation

HRID 1900100 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.[S:9]1[CH2:15][C:13](=[O:14])[NH:12][C:10]1=[S:11].C([O-])(=O)C.[Na+].O>C(O)(=O)C>[CH3:1][C:2]1[O:6][C:5]([CH:7]=[C:15]2[S:9][C:10](=[S:11])[NH:12][C:13]2=[O:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 120975-MethylfurfuralHCID 517045Sodium AcetateHCID 1201546Rhodanine

Product 1

HCID 34209754-Thiazolidinone,5-[(5-methyl-2-furanyl)methylene]-2-thioxo-Yield 89.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5.51 g (50.0 mmol) of 5-methylfuran-2-carboxaldehyde (purchased from Wako Junyaku Kogyo), 6.66 g (50.0 mmol) of rhodanine (purchased from Tokyo Kasei) 12.3 g (150 mmol) of anhydrous sodium acetate (purchased from Kokusan Kagaku) in 35 ml of acetic acid (purchased from Wako Junyaku Kogyo) was refluxed for 30 minutes, cooled and added to 500 ml of water, and the precipitate was collected, washed with water, ethanol and ether in order and dried to give 10.04 g (yield: 89.1%) of of (5-methylfurfurylidene)rhodanine as an orange brown crystalline.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. temperaturecooled
  3. customthe precipitate was collected
  4. washwashed with water, ethanol and ether in order
  5. customdried

Sources & evidence

ORD record
ord-f96be1684e804958a0a5edce17092d38
Source dataset
uspto-grants-1996_11
Patent number
US05574062

Reaction notes

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