Toluene → HCID 54417945, compound

HRID 330531Notes

Reaction equation

HRID 330531 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](=O)[CH2:21][CH2:22]C)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17].[C:25]([O-])(=O)C.[NH4+].C1(C)C=CC=CC=1>O>[CH2:20]([C:19](=[CH:18][C:12]1[CH:13]=[CH:14][C:15]([O:16][CH3:17])=[C:10]([O:9][CH3:8])[CH:11]=1)[CH:25]=[C:7]1[S:1][C:2](=[S:3])[NH:4][C:5]1=[O:6])[CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 1140TolueneHCID 517165Ammonium AcetateHCID 1201546RhodanineHCID 54183886HCID 54183886, compound

Product 1

HCID 54417945HCID 54417945, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.46 g (0.011 mol) of rhodanine, 2.34 g (0.01 mol) of 1-(3,4-dimethoxyphenyl)-1-hexen-3-one, 0.77 g (0.01 mol) of ammonium acetate and 20 ml of toluene was heated under reflux for 8 hours. After cooling, 100 of water were added to the reaction mixture, and the layers were then extracted with chloroform (80 ml×3). A chloroform layer was washed twice with water and once with a saturated aqueous solution of sodium chloride. The chloroform layer was dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure to give a reddish brown oily substance. The oily substance was purified by silica gel column chromatography (eluent, chloroform:methanol=150:1) to give 0.03 g of the isomer A of the desired 5-(α-propyl-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 8 hours
  3. temperatureAfter cooling
  4. extractionthe layers were then extracted with chloroform (80 ml×3)
  5. washA chloroform layer was washed twice with water and once with a saturated aqueous solution of sodium chloride
  6. dry with materialThe chloroform layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customto give a reddish brown oily substance
  10. customThe oily substance was purified by silica gel column chromatography (eluent, chloroform:methanol=150:1)

Sources & evidence

ORD record
ord-d943cb7034fe48f48d86b5a0cc3fa67e
Source dataset
uspto-grants-1990_01
Patent number
US04897406

Reaction notes

Loading…