Trifluoroacetic anhydride → 5-[1-(Methylsulfonimidoyl)ethyl]-2-(trifluoromethyl)pyridine

HRID 1925480ノート

反応式

HRID 1925480 の反応式
C[CH2:2][CH:3]([S:14]([O-:18])=[N:15]C#N)[C:4]1[CH:5]=[N:6][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:9]=1.F[C:20](F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH3:20][S:14]([CH:3]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[N:6][CH:5]=1)[CH3:2])(=[NH:15])=[O:18]

参加物

5

反応物 3

HCID 9845Trifluoroacetic anhydrideHCID 11430Potassium CarbonateHCID 86633708HCID 86633708、化合物

生成物 1

HCID 592186285-[1-(Methylsulfonimidoyl)ethyl]-2-(trifluoromethyl)pyridine収率 77.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

To a stirred solution of methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-λ4-sulfanylidenecyanamide (5 g, 18 mmol) in CH2Cl2 (300 mL) at 0° C. was added trifluoroacetic anhydride (7.5 mL, 54 mmol). The mixture was allowed to react at 25° C. until the starting material was fully consumed. The reaction mixture was concentrated in vacuo, dissolved in methanol (125 mL) and treated with potassium carbonate (12.5 g, 90 mmol). The mixture was allowed to stir at 25° C. until the starting material was consumed. The crude reaction mixture was filtered, concentrated and purified by chromatography (acetone-hexanes) to furnish 5-[1-(methylsulfonimidoyl)ethyl]-2-(trifluoromethyl)pyridine as a white solid (3.5 g, 77%): ESIMS m/z 253 ([M+H]+).

後処理

  1. customto react at 25° C. until the starting material
  2. customwas fully consumed
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutiondissolved in methanol (125 mL)
  5. customwas consumed
  6. customThe crude reaction mixture
  7. filtrationwas filtered
  8. concentrationconcentrated
  9. custompurified by chromatography (acetone-hexanes)

出典と根拠

ORDレコード
ord-096c41df65814f419a63e0e413e47d4e
出典データセット
uspto-grants-2012_05
特許番号
US08178685B2

反応ノート

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