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

HRID 1925480노트

반응식

HRID 1925480 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-096c41df65814f419a63e0e413e47d4e
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178685B2

반응 노트

불러오는 중…