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

HRID 279099
ノート
印刷プレビュー

反応式

HRID 279099 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180
Acetone
溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-a5adb4c5eb6b4c8486c0ee56cbd5c63b
出典データセット
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06362205B1

反応ノート

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