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

HRID 2094822노트

반응식

HRID 2094822 반응식
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]

참가 물질

5

반응물 3

HCID 9845Trifluoroacetic anhydrideHCID 11430Potassium CarbonateHCID 86633708HCID 86633708, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

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]+).

후처리

  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)

출처 및 근거

ORD 기록
ord-9e135b75f11b4af4ab2fbe9ced735b7c
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445689B2

반응 노트

불러오는 중…