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

HRID 409936

반응식

HRID 409936 반응식
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.Br[CH2:18][C:19]([OH:21])=O.Cl.[C:23](=[S:25])=[S:24]>C(OCC)(=O)C>[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[N:4]1[C:19](=[O:21])[CH2:18][S:25][C:23]1=[S:24]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 6348Carbon DisulfideHCID 72502,4-DimethylanilineHCID 8471Triethylamine

생성물 1

HCID 19078563-(2,4-Dimethyl-phenyl)-2-thioxo-thiazolidin-4-one

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0b10980121a141bf922a51ef83b85ead
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759536B2

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