Dibromomethane → 1-(4-Chlorophenyl)-2-(1,3-dithietan-2-ylidene)-2-(4-pyridinyl)ethanone

HRID 861081노트

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HRID 861081 반응식
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[O:9])=[CH:3][CH:2]=1.BrCBr.[C:20](=[S:22])=[S:21].[C:23](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:16][C:13]1[CH:12]=[CH:11][C:10]([C:8](=[O:9])[C:7](=[C:20]2[S:22][CH2:23][S:21]2)[C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:15][CH:14]=1

참가 물질

6

반응물 4

HCID 3024DibromomethaneHCID 6348Carbon Disulfide2회HCID 11430Potassium Carbonate2회HCID 103990241-(4-Chloro-phenyl)-2-pyridin-4-YL-ethanone

생성물 1

HCID 155168911-(4-Chlorophenyl)-2-(1,3-dithietan-2-ylidene)-2-(4-pyridinyl)ethanone수율 81.7%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of 2-(4-pyridyl)-1-(4-chlorophenyl)ethanone (70.0 g, 0.3 mol) prepared in a similar manner as the compound of Step 1 of Example A-19, dibromomethane (200 mL) and carbon disulfide (25.9 g, 0.34 mol) in acetone (800 mL) was added potassium carbonate (83.0 g, 0.6 mol). The reaction mixture was stirred at room temperature for 24 hours. An additional two equivalents of potassium carbonate and one equivalent of carbon disulfide was added and the stirring was continued for another 24 hours. Solvent was removed and the residue was partitioned between dichloromethane and water. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude was stirred with 1000 mL of a mixture of ethyl acetate and ether (1:9) to give 78.4 g of pure product, 1-(4-chlorophenyl)-2-(1,3-dithietan-2-ylidene)-2-(7-pyridinyl)ethanone, as a yellow solid (82%), mp: 177–179° C. Anal. Calc'd. for C15H10ClNOS2: C, 56.33; H, 3.15; N, 4.38. Found: C, 55.80; H, 2.84; N, 4.59.

후처리

  1. waitthe stirring was continued for another 24 hours
  2. customSolvent was removed
  3. customthe residue was partitioned between dichloromethane and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. stirringthe crude was stirred with 1000 mL of a mixture of ethyl acetate and ether (1:9)

출처 및 근거

ORD 기록
ord-da1dabfd872f4f7da7c411bc145a13c1
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153959B2

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