Hexa-2,4-dienal → HCID 57037858, compound

HRID 64686

Reaction equation

HRID 64686 reaction equation
[C:1]([CH2:4][N:5]1[C:9](=[O:10])[CH2:8][S:7][C:6]1=[S:11])([OH:3])=[O:2].[CH:12](=O)[CH:13]=[CH:14][CH:15]=[CH:16][CH3:17].C([O-])(=O)C.[Na+]>C(O)(=O)C>[C:1]([CH2:4][N:5]1[C:9](=[O:10])[C:8](=[CH:12][CH:13]=[CH:14][CH:15]=[CH:16][CH3:17])[S:7][C:6]1=[S:11])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 8901Hexa-2,4-dienalHCID 797933-Thiazolidineacetic acid, 4-oxo-2-thioxo-HCID 517045Sodium Acetate

Product 1

HCID 57037858HCID 57037858, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4 Grams (0.021 mole) of 3-carboxymethylrhodanine was dissolved into 30 ml of acetic acid. To the solution were added 2 g (0.021 mole) of hexa-2,4-dienal and 3.8 g (0.046 mole) of sodium acetate, and the resultant was stirred under mild reflux for 5 hours. The obtained black reaction mixture was concentrated to about one-half its initial volume under reduced pressure. The residual mixture was poured into water to form precipitate. The precipitate was extracted with ethyl acetate and the extract was recrystallized from a mixed solvent of methylene chloride and ethyl acetate to give 4.1 g of 3-carboxymethyl-5-(2,4-hexadienylidene)rhodanine in the form of yellow prism (yield: 73%).

Workup

  1. temperatureunder mild reflux for 5 hours
  2. concentrationThe obtained black reaction mixture was concentrated to about one-half its initial volume under reduced pressure
  3. additionThe residual mixture was poured into water
  4. customto form precipitate
  5. extractionThe precipitate was extracted with ethyl acetate
  6. customthe extract was recrystallized from a mixed solvent of methylene chloride and ethyl acetate

Sources & evidence

ORD record
ord-30b2acfd4f464c638cecef9fff7b12cb
Source dataset
uspto-grants-1986_09
Patent number
US04609736

Linked notes

Loading…