Methyl iodide → 2-(4-Chlorophenylsulfonyl)-3-(3,5-dimethoxyphenylamino)-3-methylsulfanyl-2-propenenitrile

HRID 840212

反応式

HRID 840212 の反応式
[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

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1454223,5-Dimethoxyphenyl isothiocyanateHCID 7358292-(4-Chlorobenzenesulfonyl)acetonitrile

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-781fcfd5ea5945398c9d554b3fdb04e0
出典データセット
uspto-grants-2002_04
特許番号
US06365609B1

関連ノート

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