Methyl iodide → 2-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-methylsulfanyl-2-propenenitrile

HRID 840234

反応式

HRID 840234 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(=O)([O-])[O-].[K+].[K+].[C:20]([C:22]1[CH:23]=[C:24]([N:28]=[C:29]=[S:30])[CH:25]=[CH:26][CH:27]=1)#[N:21].[CH3:31]I>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11](=[C:29]([NH:28][C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([C:20]#[N:21])[CH:23]=2)[S:30][CH3:31])[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 765783-Cyanophenyl isothiocyanateHCID 7358292-(4-Chlorobenzenesulfonyl)acetonitrile

生成物 1

HCID 701506282-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-methylsulfanyl-2-propenenitrile収率 96.2%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A solution of 4-chlorophenylsulfonylacetonitrile (1.0 g, 4.64 mmol) in dry acetone (10 ml) was stirred while dry potassium carbonate (1.28 g, 9.28 mmol) and 3-cyanophenyl isothiocyanate (0.78 g, 4.87 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 20 h. Excess of potassium carbonate was filtered off, methyl iodide (0.859 ml, 13.9 mmol) was added to the filtrate, and stirring was continued for 3 h. The mixture was evaporated and the residue was dissolved in dichloromethane and extracted with water and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated to afford 1.74 g (96%) of the title compound as golden brown crystals. Mp 168-170° C. 1H NMR (200 MHz, CDCl3): δ=2.22 (s, 3H), 7.50-7.68 (m, 6H), 7.84-7.93(m, 2H),9.89 (br s, 1H).

後処理

  1. additionwere added
  2. filtrationExcess of potassium carbonate was filtered off
  3. stirringstirring
  4. waitwas continued for 3 h
  5. customThe mixture was evaporated
  6. dissolutionthe residue was dissolved in dichloromethane
  7. extractionextracted with water and brine
  8. dry with materialThe organic phase was dried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated

出典と根拠

ORDレコード
ord-dd63cd7f73a14cf2b87747e6c506376d
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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