Acetone → 3-(Benzo[1,3]dioxol-5-ylamino)-2-(2,2-dimethyl-propionyl)-3-methylsulfanyl-propenenitrile

HRID 279124

反応式

HRID 279124 の反応式
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=[O:7])[CH2:4][C:5]#[N:6].[CH3:10]C(C)=O.[CH2:14]1[O:22][C:21]2[CH:20]=[CH:19][C:18]([N:23]=[C:24]=[S:25])=[CH:17][C:16]=2[O:15]1.CI>>[O:22]1[C:21]2[CH:20]=[CH:19][C:18]([NH:23][C:24]([S:25][CH3:10])=[C:4]([C:3](=[O:7])[C:2]([CH3:9])([CH3:8])[CH3:1])[C:5]#[N:6])=[CH:17][C:16]=2[O:15][CH2:14]1

参加物

5

反応物 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 1235931,3-Benzodioxole, 5-isothiocyanato-

生成物 1

HCID 701509263-(Benzo[1,3]dioxol-5-ylamino)-2-(2,2-dimethyl-propionyl)-3-methylsulfanyl-propenenitrile収率 98%

実験手順

To a solution of 4,4-dimethyl-3-oxopentanenitrile (0.626 g, 5.0 mmol) in dry acetone (10 ml) first potassium carbonate (1.38 g, 10 mmol) and then 3,4-methylendioxyphenyl isothiocyanate (0.941 g, 5.3 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 72 h, and then filtered. To the filtrate methyl iodide (0.93 ml, 15 mmol) was added. The mixture was stirred at room temperature for 45 min. The precipitate was filtered off and 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/heptane 1:1 gave 1.56 g (98%) of the title compound. Mp 139-141° C.; 1H NMR (200 MHz, CDCl3): δ=1.40 (s, 9H), 2.28 (s, 3H), 6.03 (s, 2H), 6.75 (dd, 1H), 6.8 (m, 2H), 13.5 (br s, 1H); EI SP/MS: 318 (M+).

後処理

  1. filtrationfiltered
  2. stirringThe mixture was stirred at room temperature for 45 min
  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/heptane 1:1

出典と根拠

ORDレコード
ord-fb83ddcdc19643daabce61aa4109f2a6
出典データセット
uspto-grants-2002_03
特許番号
US06362205B1

関連ノート

読み込み中…