碘甲烷 → 2-(4-Chlorophenylsulfonyl)-3-(3,5-dimethoxyphenylamino)-3-methylsulfanyl-2-propenenitrile

HRID 840212

反应方程式

HRID 840212 反应方程式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]#[N:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:14](=O)([O-])[O-].[K+].[K+].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([N:30]=[C:31]=[S:32])[CH:25]=[C:26]([O:28][CH3:29])[CH:27]=1.CI>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11](=[C:31]([NH:30][C:24]2[CH:25]=[C:26]([O:28][CH3:29])[CH:27]=[C:22]([O:21][CH3:20])[CH:23]=2)[S:32][CH3:14])[C:12]#[N:13])(=[O:9])=[O:10])=[CH:6][CH:7]=1

参与物

6

反应物 4

HCID 6328碘甲烷HCID 11430碳酸钾HCID 1454223,5-二甲氧基苯基异硫氰酸酯HCID 735829(4-氯苯磺酰)乙腈

产物 1

HCID 701503682-(4-Chlorophenylsulfonyl)-3-(3,5-dimethoxyphenylamino)-3-methylsulfanyl-2-propenenitrile收率 65%

试剂、催化剂与溶剂 1

HCID 180丙酮溶剂

实验过程

To a solution of 4-chlorophenylsulfonylacetonitrile (1.00 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 2 h 15 min and then filtered. 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 concentrated. The residue was dissolved in DCM, washed with water, dried (Na2SO4) and concentrated. The residue was crystallised from ethyl acetate/heptane 1:2 to give 1.27 g (65%) of the title compound. Mp 119.5-123° C.; 1H NMR (200 MHz, CDCl3): δ=2.29 (s, 3H), 3.80 (s, 6H), 3.36 (m, 3H), 7.53 (d, 2H), 7.87 (d, 2H), 9.82 (br s, 1H); EI SP/MS: 424 (M+).

后处理

  1. filtrationfiltered
  2. stirringThe mixture was stirred at room temperature for 4 h
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionThe residue was dissolved in DCM
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was crystallised from ethyl acetate/heptane 1:2

来源与证据

ORD记录
ord-781fcfd5ea5945398c9d554b3fdb04e0
来源数据集
uspto-grants-2002_04
专利号
US06365609B1

关联笔记

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