Acetone → 2-Isopropylsulfonyl-3-(3-methoxyphenylamino)-3-methylsulfanyl-2-propenenitrile

HRID 279132

反応式

HRID 279132 の反応式
C([S:4]([CH2:7][C:8]#[N:9])(=[O:6])=[O:5])CC.C(=O)([O-])[O-].[K+].[K+].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([N:24]=[C:25]=[S:26])[CH:21]=[CH:22][CH:23]=1.[CH3:27]I.[CH3:29][C:30]([CH3:32])=O>>[CH:30]([S:4]([C:7](=[C:25]([NH:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([O:17][CH3:16])[CH:19]=1)[S:26][CH3:27])[C:8]#[N:9])(=[O:6])=[O:5])([CH3:32])[CH3:29]

参加物

6

反応物 5

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1378323-Methoxyphenyl isothiocyanateHCID 5194412-(Propane-1-sulfonyl)acetonitrile

生成物 1

HCID 701495792-Isopropylsulfonyl-3-(3-methoxyphenylamino)-3-methylsulfanyl-2-propenenitrile収率 99%

実験手順

A solution of 2-propanesulfonylacetonitrile (2.0 g, 13.6 mmol) in dry acetone (25 ml) was stirred while dry potassium carbonate (1.28 g, 9.28 mmol) and 3-methoxyphenyl isothiocyanate (2.36 g, 14.3 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 (2.54 ml, 40.8 mmol) was added to the filtrate, and stirring was continued for 60 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 4.40 g (99%) of the title compound as yellow crystals. Mp 107-110° C. 1H NMR (200 MHz, CDCl3): δ=1.44 (d, 6H), 2.22 (s, 3H), 3.36 (heptet, 1H), 3.83 (s, 3H), 6.81 (m, 1H), 6.85 (dd, 1H), 6.87 (dd, 1H), 7.32 (dd, 1H), 9.91 (br s, 1H).

後処理

  1. additionwere added
  2. filtrationExcess of potassium carbonate was filtered off
  3. stirringstirring
  4. waitwas continued for 60 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-2c7e2b5e9ea945faa2c9111ef17e37ca
出典データセット
uspto-grants-2002_03
特許番号
US06362205B1

関連ノート

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