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

HRID 861081ノート

反応式

HRID 861081 の反応式
[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

参加物

6

反応物 4

HCID 3024DibromomethaneHCID 6348Carbon Disulfide2 回HCID 11430Potassium Carbonate2 回HCID 103990241-(4-Chloro-phenyl)-2-pyridin-4-YL-ethanone

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-da1dabfd872f4f7da7c411bc145a13c1
出典データセット
uspto-grants-2006_12
特許番号
US07153959B2

反応ノート

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