Methyl iodide → 3-(4-Chlorophenylamino)-2-methylsulfonyl-3-methylsulfanyl-propenenitrile

HRID 279121

반응식

HRID 279121 반응식
[CH3:1][S:2]([CH2:5][C:6]#[N:7])(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[S:23])=[CH:17][CH:16]=1.[CH3:24]I>CC(C)=O>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([S:23][CH3:24])=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C:6]#[N:7])=[CH:17][CH:16]=1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 164804-Chlorophenyl isothiocyanateHCID 75283(Methylsulfonyl)acetonitrile

생성물 1

HCID 701491873-(4-Chlorophenylamino)-2-methylsulfonyl-3-methylsulfanyl-propenenitrile수율 80%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of methanesulfonylacetonitrile (0.55 g, 4.9 mmol) in dry acetone (5 ml) first dry potassium carbonate (1.28 g, 9.3 mmol) and then 4-chlorophenyl isothiocyanate (0.78 g, 4.6 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 22 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 precipitate was filtered off, the filtrate was concentrated. The residue was taken up into dichloromethane and water. The organic layer was washed with water (2×), dried (sodium sulfate) and concentrated. Crystallisation from ethyl acetate gave 1.114 g (80%) of the title compound. 1H NMR (200 MHz, CDCl3): δ=2.25 (s, 3H), 3.20 /s, 3H), 7.25 (d, 2H), 7.41 (d, 2H), 9.70 (br s, 1H); EI SP/MS: 302 (M+), 304 (M+2).

후처리

  1. filtrationfiltered
  2. stirringThe mixture was stirred at room temperature for 2 h
  3. filtrationThe precipitate was filtered off
  4. concentrationthe filtrate was concentrated
  5. washThe organic layer was washed with water (2×)
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated
  8. customCrystallisation from ethyl acetate

출처 및 근거

ORD 기록
ord-de3b83c3a84c43fdb7fa43ff3ffe98fc
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362205B1

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