Water → HCID 22007864, compound

HRID 323928Notes

Reaction equation

HRID 323928 reaction equation
[CH:1](=[O:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[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>[S:8]1[CH2:14][C:12](=[O:13])[NH:11][C:9]1=[S:10].[CH:1](=[O:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7362FurfuralHCID 517045Sodium AcetateHCID 1201546Rhodanine

Product 1

HCID 22007864HCID 22007864, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
85 °C

Procedure

In 150 mL of acetic acid, were suspended 11.7 g (121 mmol) of furfural and 16.25 g (122 mmol) of rhodanine. To the suspension, was added 31.0 g (378 mmol) of sodium acetate, and the mixture was stirred at 85° C. for 1 hour and 40 min. After confirming the appearance of a bright orange precipitate, the reaction suspension was cooled to room temperature and poured into 200 mL of water. After thorough stirring, the resulting precipitate was filtered under reduced pressure, and the residue was washed with 300 mL of water, 20 mL of 99.5% ethanol, and then 10 mL of diethyl ether. The residue was dried to give 20.0 g (94.8 mmol) of furfural rhodanine with a crude yield of 78%. The furfural rhodanine was used for the subsequent reaction without being further purified.

Workup

  1. temperaturethe reaction suspension was cooled to room temperature
  2. filtrationAfter thorough stirring, the resulting precipitate was filtered under reduced pressure
  3. washthe residue was washed with 300 mL of water, 20 mL of 99.5% ethanol
  4. customThe residue was dried

Sources & evidence

ORD record
ord-305d2b3861b54134ba1f5454f76c26c3
Source dataset
uspto-grants-2001_04
Patent number
US06215016B1

Reaction notes

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