Toluene → HCID 57221314, compound

HRID 330532Notes

Reaction equation

HRID 330532 reaction equation
[S:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[S:3].O=[C:9]([CH2:21][CH2:22][CH3:23])[CH:10]=[CH:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1.C([O-])(=O)C.[NH4+].C1(C)C=CC=CC=1>C(O)(=O)C>[O:6]=[C:5]1[C:7](=[C:9]([CH2:21][CH2:22][CH3:23])[CH:10]=[CH:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)[S:1][C:2](=[S:3])[NH:4]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 517165Ammonium AcetateHCID 1201546RhodanineHCID 53796635HCID 53796635, compound

Product 1

HCID 57221314HCID 57221314, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.73 g (0.0055 mol) of rhodanine, 1.09 g (0.005mol) of 4-(3-oxo-hexen-1-yl)benzoic acid, 0.39 g (0.005 mol) of ammonium acetate and 10 ml of toluene was heated under reflux for 5 hours. After cooling, acetic acid was added to the reaction mixture and the precipitate was recovered by filtration. The precipitate was recrystallized from chloroform-methanol to give 0.10 g of the isomer A of the desired 4-[3-(4-oxo-2- thioxo-5-thiazolidinylidene)-1-hexen-1-yl]benzoic acid. To the filtrate was added water and the resulting mixture was extracted with chloroform (100 ml×3). The chloroform layer was washed three times with water and then once with a saturated aqueous solution of sodium chloride. The layer was dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent, chlorform : methanol=10:1) to give 0.10 g of the isomer B of the desired product.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitate was recovered by filtration
  5. customThe precipitate was recrystallized from chloroform-methanol

Sources & evidence

ORD record
ord-fb142dea603445bba478152d35a41779
Source dataset
uspto-grants-1990_01
Patent number
US04897406

Reaction notes

Loading…