Triethylamine → 6,7-Dimethyl-5-methoxy-3-(methylthio)-1,3-dihydro-2H-indole-2-one

HRID 1743396

반응식

HRID 1743396 반응식
[CH3:1][S:2][CH2:3][C:4]([O:6]C)=O.S(Cl)(Cl)(=O)=O.[CH3:13][O:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[C:17]([CH3:22])[C:16]=1[CH3:23].CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.C(N(CC)CC)C>ClCCl.O>[CH3:23][C:16]1[C:17]([CH3:22])=[C:18]2[C:20]([CH:3]([S:2][CH3:1])[C:4](=[O:6])[NH:19]2)=[CH:21][C:15]=1[O:14][CH3:13]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 85522Methyl (methylthio)acetateHCID 88675Proton spongeHCID 110948094-Methoxy-2,3-dimethylaniline

생성물 1

HCID 222380776,7-Dimethyl-5-methoxy-3-(methylthio)-1,3-dihydro-2H-indole-2-one수율 46%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of methyl (methylthio)acetate (40.8 mL, 317 mmol) in dichloromethane (1100 mL) was added sulfuryl chloride (26.6 mL, 331 mmol) at −78° C., and the mixture was stirred for 15 minutes. Further, a solution of 4-methoxy-2,3-dimethylaniline (41.7 g, 276 mmol) and proton sponge (62.1 g, 290 mmol) in dichloromethane (200 mL) was added dropwise over 1 hour and mixture was stirred at the same temperature for 1 hour. Triethylamine (43 mL, 380 mmol) was added, and the temperature was gradually raised to room temperature. After stirring at room temperature for 2 hours, water was added, the organic layer was washed with an aqueous saturated solution of sodium bicarbonate and saturated brine, dried over sodium sulfate, and the solvent was distilled off under reduced pressure. To the residue was added toluene (300 mL), and the mixture was stirred at reflux for 1 hour. The solvent was distilled off under reduced pressure, which was recrystallized from ethyl acetate to obtain 30.0 g of the title compound.

후처리

  1. stirringmixture was stirred at the same temperature for 1 hour
  2. stirringAfter stirring at room temperature for 2 hours
  3. washthe organic layer was washed with an aqueous saturated solution of sodium bicarbonate and saturated brine
  4. dry with materialdried over sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionTo the residue was added toluene (300 mL)
  7. stirringthe mixture was stirred
  8. temperatureat reflux for 1 hour
  9. distillationThe solvent was distilled off under reduced pressure, which
  10. customwas recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-d7c675b9ee8e41cd9e3d5f36d3576b26
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07008940B1

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