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

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.

1. additionwas dropwise added to the mixture
2. additionAfter completion of the addition
3. stirringstirring
4. filtrationThe reaction mixture was filtered
5. dissolutionthe filtrate was dissolved in an aqueous sodium bicarbonate solution (NaHCO3)
6. additionmixed with 2.2
7. customThe resulting reaction mixture
8. temperatureheated for 6 hrs
9. extractionAfter extraction with methylene chloride (CH2Cl2)
10. washwashed with saturated brine
11. dry with materialdried over magnesium sulfate
12. concentrationconcentrated in vacuo
13. customPurification of the
14. concentrationconcentrate by silica gel column chromatography

ORDレコード

ord-0b10980121a141bf922a51ef83b85ead

出典データセット

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08759536B2