4-(3,4-Dimethoxyphenyl)but-3-en-2-one → HCID 54569806, compound

HRID 330528Notes

Reaction equation

HRID 330528 reaction equation
[S:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[S:3].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH:13]=[CH:14][C:15](=O)C.[C:23]([O-])(=O)C.[NH4+]>C1(C)C=CC=CC=1>[CH3:23][C:14](=[CH:13][C:12]1[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:10]([O:9][CH3:8])[CH:11]=1)[CH:15]=[C:7]1[S:1][C:2](=[S:3])[NH:4][C:5]1=[O:6]

Participants

5

Reactant 3

HCID 847484-(3,4-Dimethoxyphenyl)but-3-en-2-oneHCID 517165Ammonium AcetateHCID 1201546Rhodanine

Product 1

HCID 54569806HCID 54569806, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1.73 g (0.013 mol) of rhodanine, 2.06 g (0.01 mol) of 3,4-dimethoxybenzalacetone, 0.31 g (0.004 mol) of ammonium acetate and 5 ml of toluene was heated under reflux for 2 hours. After cooling, precipitates were recovered by filtration and washed with methanol. The residue was purified by silica gel column chromatography (eluent, chloroform) to obtain 0.5 g of the isomer A of the desired 5-(α-methyl-3,4-dimethoxycinnamylidene)-4-oxo-2-thioxothiazolidine from the first eluate and 0.2 g of the isomer B from the subsequent eluate.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. customprecipitates
  5. filtrationwere recovered by filtration
  6. washwashed with methanol
  7. customThe residue was purified by silica gel column chromatography (eluent, chloroform)

Sources & evidence

ORD record
ord-1ae84a9199614190a66c75abb123fba9
Source dataset
uspto-grants-1990_01
Patent number
US04897406

Reaction notes

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