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

HRID 279121

反応式

HRID 279121 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-de3b83c3a84c43fdb7fa43ff3ffe98fc
出典データセット
uspto-grants-2002_03
特許番号
US06362205B1

関連ノート

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