Methyl iodide → 3-(3,5-Bis(trifluoromethyl)phenylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrile

HRID 279099

반응식

HRID 279099 반응식
[CH3:1][S:2]([CH2:5][C:6]#[N:7])(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].[F:14][C:15]([F:30])([F:29])[C:16]1[CH:17]=[C:18]([N:26]=[C:27]=[S:28])[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1.[CH3:31]I>CC(C)=O>[F:23][C:22]([F:24])([F:25])[C:20]1[CH:19]=[C:18]([NH:26][C:27]([S:28][CH3:31])=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C:6]#[N:7])[CH:17]=[C:16]([C:15]([F:29])([F:14])[F:30])[CH:21]=1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 75283(Methylsulfonyl)acetonitrileHCID 27333953,5-Bis(trifluoromethyl)phenyl isothiocyanate

생성물 1

HCID 739865843-(3,5-Bis(trifluoromethyl)phenylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrile수율 83.3%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of methanesulfonylacetonitrile (0.55 g, 4.6 mmol) in dry acetone (10 ml) first dry potassium carbonate (1.28 g, 9.3 mmol) and then 3,5-bis(trifluoromethyl)phenyl isothiocyanate (1,32 g, 4.7 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 4 h, and then filtered. To the filtrate methyl iodide (0.86 ml, 13.9 mmol) was added. The mixture was stirred at room temperature for 2 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried (sodium sulfate) and concentrated. The residue was recrystallised from ethyl acetate/heptane 1:2 to give the title compound (1.55 g, 83%). Mp 129-131° C. 1H NMR (200 MHz, CDCl3): δ=2.35 (s, 3H), 3.25 (s, 3H), 7.77 (s, 2H), 7.80 (s, 1H)H), 9.90 (br s, 1H); EI SP/MS: 404 (M+).

후처리

  1. filtrationfiltered
  2. stirringThe mixture was stirred at room temperature for 2 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washwashed with water
  7. dry with materialThe organic layer was dried (sodium sulfate)
  8. concentrationconcentrated
  9. customThe residue was recrystallised from ethyl acetate/heptane 1:2

출처 및 근거

ORD 기록
ord-a5adb4c5eb6b4c8486c0ee56cbd5c63b
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362205B1

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