Hydrochloric Acid → 3-(2,4-Dimethyl-phenyl)-2-thioxo-thiazolidin-4-one

Beteiligte Stoffe

Reaktionsschritte

At 0° C., 1 g of 2,4-dimethylaniline (8.04 mmol) was mixed with 54 mL of a 0.2 M solution of triethylamine in ethyl acetate, and 0.65 mL of a carbon disulfide (CS2) solution was dropwise added to the mixture with slowly stirring. After completion of the addition, stirring was continued for an additional 12 hrs. The reaction mixture was filtered, and the filtrate was dissolved in an aqueous sodium bicarbonate solution (NaHCO3) and mixed with 2.2. g of bromoacetic acid (15.83 mmol) for 2 hrs by stirring. The resulting reaction mixture was acidified (pH 2) with a 35% HCl solution and heated for 6 hrs. After extraction with methylene chloride (CH2Cl2), the organic layer was pooled, washed with saturated brine, dried over magnesium sulfate, and concentrated in vacuo. Purification of the concentrate by silica gel column chromatography afforded the title compound.

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