Toluene → HCID 57230200, compound

HRID 1196963Notes

Reaction equation

HRID 1196963 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][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17].C([O-])(=O)C.[NH4+].C1(C)C=CC=CC=1>C(OCC)(=O)C.O>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][C:20](=[C:7]2[S:1][C:2](=[S:3])[NH:4][C:5]2=[O:6])[CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

7

Reactant 4

HCID 1140TolueneHCID 517165Ammonium AcetateHCID 1201546RhodanineHCID 54383002HCID 54383002, compound

Product 1

HCID 57230200HCID 57230200, compoundYield 11.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.60 g (0.012 mol) of rhodanine, 3.06 g (0.01 mol) of ethyl 7-(3,4-dimethoxyphenyl)-5-oxo-6-heptenoate, 0.77 g (0.01 mol) of ammonium acetate and 20 ml of toluene was heated under reflux for 8 hours. After cooling, 100 ml of water were added to the reaction mixture d with ethyl acetate (3×100 ml). The ethyl acetate layer was washed three times with water and once with a saturated saline solution, dried over magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to afford a reddish brown oily substance. The oily substance was purified by silica gel column chromatography (eluent, chloroform) to obtain 0.5 g of ethyl 7-(3,4-dimethoxyphenyl)-5-(4-oxo-2-thioxo-5-thiazolidinylidene)-6-heptenoate. To 0.21 g of this compound was added 5 ml of water and 1 ml of 5% sodium hydroxide solution and the mixture was stirred at room temperature for 3 hours. This mixture was acidified with 10% hydrochloric acid, 100 ml of water was added to the acidified mixture which was extracted with ethyl acetate (3 ×120 ml). The ethyl acetate layer was washed three times with water and once with saturated saline solution, dried over magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, chloroform : methanol ™10:1) to obtain 0.12 g of Isomer A of 7-(3,4-dimethoxyphenyl)-5-(4-oxo-2-thioxo-5-thiazolidinylidene)-6-heptenoic acid from the first eluate and 0.03 g of Isomer B from the subsequent eluate.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hours
  3. temperatureAfter cooling
  4. washThe ethyl acetate layer was washed three times with water
  5. dry with materialonce with a saturated saline solution, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customto afford a reddish brown oily substance
  9. customThe oily substance was purified by silica gel column chromatography (eluent, chloroform)

Sources & evidence

ORD record
ord-93c2643959ec4adc8d4bfd7698994b09
Source dataset
uspto-grants-1992_05
Patent number
US05116855

Reaction notes

Loading…