Methyl iodide → 1-Cyano-3-methylthio-4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[c]thiophene

HRID 1385293노트

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HRID 1385293 반응식
[C:1]1(=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][C:3](=O)[CH2:2]1.[H-].[Na+].[C:12](=[S:14])=[S:13].[CH3:15]I.Br[CH2:18][C:19]#[N:20]>CN(C=O)C.O>[C:19]([C:18]1[S:13][C:12]([S:14][CH3:15])=[C:2]2[C:1](=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=12)#[N:20]

참가 물질

8

반응물 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 4072367Cycloheptane-1,3-dione

생성물 1

HCID 211845001-Cyano-3-methylthio-4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[c]thiophene수율 32%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

Cycloheptan-1,3-dione (0.5 g, 4 mmol) was dissolved in DMF (10 mL) and cooled to 0° C. Sodium hydride (0.48 g of 60% dispersion in oil, 12 mmol) was added and the suspension stirred at 0-5° C. for 30 min. Carbon disulphide (0.45 g, 6 mmol) was added in one portion and the solution was stirred at 0-5° C. for 30 min. Methyl iodide (0.66 g, 4.4 mmol) was added in one portion and the mixture stirred at room temperature for 30 min. After cooling to 0-5° C., bromoacetonitrile (0.27 mL, 4.4 mmol) was added in one portion and the mixture was stirred at room temperature for 30 min. The mixture was then poured into water, extracted with ethyl acetate and the extracts dried (Na2SO4). After evaporating to dryness, the residue was purified by chromatographed on silica gel, eluting with ethyl acetate:hexane (1:4) to yield the title compound as a pale yellow solid (280 mg, 32%). 1HNMR (360 MHz, CDCl3) δ 1.88-1.96 (4H, m), 2.60 (3H, s), 2.75-2.78 (2H, m), 3.21-3.24 (2H, m). MS (ES+) 296 (M+1).

후처리

  1. stirringthe solution was stirred at 0-5° C. for 30 min
  2. stirringthe mixture stirred at room temperature for 30 min
  3. temperatureAfter cooling to 0-5° C.
  4. stirringthe mixture was stirred at room temperature for 30 min
  5. extractionextracted with ethyl acetate
  6. dry with materialthe extracts dried (Na2SO4)
  7. customAfter evaporating to dryness
  8. customthe residue was purified
  9. customby chromatographed on silica gel
  10. washeluting with ethyl acetate:hexane (1:4)

출처 및 근거

ORD 기록
ord-ff07417bf9da4454a823c9f7c14b48d3
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06262103B1

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