Methyl iodide → HCID 18314021, 화합물

HRID 277006

반응식

HRID 277006 반응식
[CH3:1][C:2](=O)[CH2:3][C:4](=O)[CH2:5][CH2:6][CH3:7].[OH-:10].[K+].[C:12](=[S:14])=[S:13].Cl[CH2:16][C:17]#[N:18].[C:19](=O)([O-])[O-].[K+].[K+].CI>CS(C)=O.O>[CH2:2]([C:3]1[C:4]([C:5](=[O:10])[CH2:6][CH3:7])=[C:12]([S:14][CH3:19])[S:13][C:16]=1[C:17]#[N:18])[CH3:1]

참가 물질

9

반응물 6

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 237322,4-Heptanedione

생성물 1

HCID 18314021HCID 18314021, 화합물수율 88.1%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 962Water용매

실험 절차

To a solution containing 2,4-heptanedione (10.0 g, 78.0 mmol) in dimethyl sulfoxide (100 ml) were added dropwise under ice-cooling an 85% solution containing potassium hydroxide (10.3 g, 156.0 mmol) in water (10 ml) and carbon disulfide (5.9 g, 78.0 mmol) in turn, and then the mixture was stirred at that temperature for 30 minutes. Subsequently, a solution containing chloroacetonitrile (5.3 g, 70.2 mmol) in dimethyl sulfoxide (10 ml) was added dropwise under ice-cooling over 5 minutes and the mixture was stirred at that temperature for 20 minutes. Potassium carbonate (10.8 g, 78.0 mmol) and methyl iodide (12.2 g, 85.8 mmol) were then added and the mixture was stirred further for 30 minutes. The reaction solution was extracted 10 with ethyl acetate, and the organic layer was washed (with water and aqueous saturated sodium chloride, in turn), dried (over anhydrous magnesium sulfate), filtered and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=10:1) and the crystals thus obtained were washed with n-hexane to afford 3-ethyl-5-methylthio-4-propionylthiophene-2-carbonitrile (14.8 g, 88%) as colorless prisms.

후처리

  1. additionwere added dropwise under ice-
  2. additionwas added dropwise under ice-
  3. temperaturecooling over 5 minutes
  4. stirringthe mixture was stirred at that temperature for 20 minutes
  5. stirringthe mixture was stirred further for 30 minutes
  6. extractionThe reaction solution was extracted 10 with ethyl acetate
  7. washthe organic layer was washed (with water and aqueous saturated sodium chloride, in turn)
  8. dry with materialdried (over anhydrous magnesium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue thus obtained
  12. customwas purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=10:1)
  13. customthe crystals thus obtained
  14. washwere washed with n-hexane

출처 및 근거

ORD 기록
ord-f20786026f874d0ca04ebab86957f32f
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355663B1

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