Triethylamine → 4,7-Dimethyl-5-methoxy-3-(methylthio)-1,3-dihydro-2H-indol-2-one

HRID 985593

반응식

HRID 985593 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[C:21]([CH3:22])=[CH:20][C:18]([NH2:19])=[C:17]([CH3:23])[CH:16]=1.CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.C(N(CC)CC)C>ClCCl.O>[CH3:22][C:21]1[C:15]([O:14][CH3:13])=[CH:16][C:17]([CH3:23])=[C:18]2[C:20]=1[CH:3]([S:2][CH3:1])[C:4](=[O:6])[NH:19]2

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 85522Methyl (methylthio)acetateHCID 88675Proton spongeHCID 225068644-Methoxy-2,5-dimethylaniline

생성물 1

HCID 225068774,7-Dimethyl-5-methoxy-3-(methylthio)-1,3-dihydro-2H-indol-2-one수율 77.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of methyl (methylthio)acetate (14.8 ml, 115 mmol) in dichloromethane (400 ml) was added sulfuryl chloride (9.64 ml, 120 mmol) at −78° C. and stirred for 15 minutes. To the mixture was added dropwise a solution of 4-methoxy-2,5-dimethylaniline (15.1 g, 100 mmol) and proton sponge (22.5 g, 105 mmol) in dichloromethane (100 ml) over 1 hour and the mixture was stirred at the same temperature for 1 hour. Then, triethylamine (15.3 ml, 110 mmol) was added, and the mixture was allowed to warm to room temperature slowly. After stirring at room temperature for 1 hour, water was added and the precipitated crystals were collected by filtration and washed with dichloromethane and water to obtain 18.3 g of the title compound.

후처리

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. stirringAfter stirring at room temperature for 1 hour
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with dichloromethane and water

출처 및 근거

ORD 기록
ord-5a37714130484af88bbda379de5341ac
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06872718B1

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