碘甲烷 → 3-(3,5-Dimethoxyphenylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrile

HRID 840223

反应方程式

HRID 840223 反应方程式
[CH3:1][S:2]([CH2:5][C:6]#[N:7])(=[O:4])=[O:3].[C:8](=O)([O-])[O-].[K+].[K+].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([N:24]=[C:25]=[S:26])[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1.CI>CC(C)=O>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([NH:24][C:25]([S:26][CH3:8])=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C:6]#[N:7])[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1

参与物

6

反应物 4

HCID 6328碘甲烷HCID 11430碳酸钾HCID 75283甲基磺酰乙腈HCID 1454223,5-二甲氧基苯基异硫氰酸酯

产物 1

HCID 701502363-(3,5-Dimethoxyphenylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrile收率 48.2%

试剂、催化剂与溶剂 1

HCID 180丙酮溶剂

实验过程

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-dimethoxyphenyl isothiocyanate (0.96 g, 4.9 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 23 h, then filtered and washed with ethanol. To the filtrate methyl iodide (0.86 ml, 13.9 mmol) was added. The mixture was stirred at room temperature for 4 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 to give the title compound (0.728 g, 48%). 1H NMR (200 MHz, CDCl3): δ=2.27 (s, 3H), 3.19 (s, 3H), (s, 3H), 3.80 (s, 6H), 6.48 (t, 1H), 6.44 (d, 2H) EI SP/MS: 328 (M+).

后处理

  1. filtrationfiltered
  2. washwashed with ethanol
  3. stirringThe mixture was stirred at room temperature for 4 h
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. dissolutionThe residue was dissolved in dichloromethane
  7. washwashed with water
  8. dry with materialThe organic layer was dried (sodium sulfate)
  9. concentrationconcentrated
  10. customThe residue was recrystallised from ethyl acetate

来源与证据

ORD记录
ord-5d27ecbf65814e65852f0893b374a07e
来源数据集
uspto-grants-2002_04
专利号
US06365609B1

关联笔记

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