Sodium methanethiolate → 6-benzyloxy-N-[5-(methylthio)pentyl]-3-nitroquinolin-4-amine

HRID 598317노트

반응식

HRID 598317 반응식
[CH3:1][S-:2].[Na+].[CH2:4]([O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[CH:17][C:16]([N+:22]([O-:24])=[O:23])=[C:15]2[NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]Cl)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CN(C=O)C>[CH2:4]([O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[CH:17][C:16]([N+:22]([O-:24])=[O:23])=[C:15]2[NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][S:2][CH3:1])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

4

반응물 2

HCID 4378561Sodium methanethiolate2회HCID 670510456-benzyloxy-N-(5-chloropentyl)-3-nitroquinolin-4-amine

생성물 1

HCID 670510536-benzyloxy-N-[5-(methylthio)pentyl]-3-nitroquinolin-4-amine수율 79.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Under a nitrogen atmosphere, solid sodium thiomethoxide (1.38 g, 18.7 mmol, 95% pure) was added to a solution of 6-benzyloxy-N-(5-chloropentyl)-3-nitroquinolin-4-amine (6.24 g, 15.6 mmol) in DMF. The reaction was stirred at ambient temperature for 30 minutes and then heated at 80° C. for one hour, at which time a yellow precipitate formed. The reaction mixture was partitioned between water (390 mL) and dichloromethane (150 mL). The aqueous layer was washed with dichloromethane (100 mL), and the combined organic fractions were washed with saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide a red oil. An analysis by nuclear magnetic resonance spectroscopy indicated the presence of a large amount of starting material. The reaction product was dissolved in DMF (78 mL), treated with sodium thiomethoxide, and heated at reflux for two hours. The work-up described above was repeated, and the crude product was purified by column chromatography on silica gel (eluting with 70:30 ethyl acetate:hexane) to provide 5.1 g of 6-benzyloxy-N-[5-(methylthio)pentyl]-3-nitroquinolin-4-amine as a yellow oil.

후처리

  1. temperatureheated at 80° C. for one hour, at which time a yellow precipitate
  2. customformed
  3. customThe reaction mixture was partitioned between water (390 mL) and dichloromethane (150 mL)
  4. washThe aqueous layer was washed with dichloromethane (100 mL)
  5. washthe combined organic fractions were washed with saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto provide a red oil
  10. temperatureheated
  11. temperatureat reflux for two hours
  12. customthe crude product was purified by column chromatography on silica gel (eluting with 70:30 ethyl acetate:hexane)

출처 및 근거

ORD 기록
ord-798f10a0b9ff4063aed1586fa1e761ce
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897597B2

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