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

HRID 840233

반응식

HRID 840233 반응식
[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

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-2d293ca67fa640d18060d813dce05ab2
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06365609B1

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