Dimethyl Sulfoxide → 3,3-Bis-methylthio-2-(2,5-dimethylbenzoyl)-acrylonitrile

HRID 1279274

反応式

HRID 1279274 の反応式
[C:1]([CH2:3][C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:7]=1[CH3:13])=[O:5])#[N:2].[C:14](=S)=[S:15].[H-].[Na+].CI.[CH3:21][S:22]([CH3:24])=O>O>[CH3:21][S:22][C:24]([S:15][CH3:14])=[C:3]([C:4](=[O:5])[C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:7]=1[CH3:13])[C:1]#[N:2]

参加物

7

反応物 5

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 158952642,5-Dimethylbenzoylacetonitrile

生成物 1

HCID 158952653,3-Bis-methylthio-2-(2,5-dimethylbenzoyl)-acrylonitrile

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
18 °C

実験手順

A solution of 4.96 g (28.6 mmol) of 2-cyano-2′,5′-dimethylacetophenone in 120 mL of dry dimethyl sulfoxide and 3.43 mL (57.3 mmol) of carbon disulfide in a flame-dried 3-neck round bottom flask under dry nitrogen was stirred at 15-18° C. while 1.41 g (58.7 mmol) of oil free sodium hydride was added in 5 portions. The resulting deep red solution was stirred for 1 hour at 18° C. and then cooled to 15° C. whereupon 3.92 mL (8.95 g, 63.0 mmol) of methyl iodide was added dropwise. The temperature rose to about 22° C. during the addition. After stirring for 2 hours at room temperature, the reaction mixture was poured into cold water and the aqueous layer was extracted three times with ethyl acetate. The combined extracts were washed three times with water and then dried with brine and magnesium sulfate. Evaporation gave 8.96 g of the title compound as a heavy orange oil which crystallized in the refrigerator. The analytical sample crystallized from ethanol, m.p. 74.5-75.5° C.

後処理

  1. additionwas added in 5 portions
  2. additionwas added dropwise
  3. additionThe temperature rose to about 22° C. during the addition
  4. stirringAfter stirring for 2 hours at room temperature
  5. extractionthe aqueous layer was extracted three times with ethyl acetate
  6. washThe combined extracts were washed three times with water
  7. dry with materialdried with brine and magnesium sulfate
  8. customEvaporation

出典と根拠

ORDレコード
ord-6b8076c7c034418a9fc9d8c133109b0c
出典データセット
uspto-grants-2002_09
特許番号
US06448265B1

関連ノート

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