Water → 1-(Methylsulfonyl)-5-nitroindoline

HRID 1398069

반응식

HRID 1398069 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7]2)([O-:3])=[O:2].[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(N(CC)CC)C.O>ClCCl>[CH3:13][S:14]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH2:7][CH2:8]1)(=[O:16])=[O:15]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471Triethylamine2회HCID 31297Methanesulfonyl chloride2회HCID 362195-Nitroindoline

생성물 1

HCID 29182131-(Methylsulfonyl)-5-nitroindoline수율 92.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 300 mg (1.83 mmol) of 5-nitroindoline in 20 mL of dichloromethane were added 141 μL (2.74 mmol) of methanesulfonyl chloride and 382 μL (2.74 mmol) of triethylamine, and the mixture was stirred for 2 hours at room temperature. 141 μL (2.74 mmol) of methanesulfonyl chloride and 255 μL (1.83 mmol) of triethylamine were further added to the reaction mixture, and the mixture was stirred for 2 hours at room temperature. Then, water was added to the reaction mixture and the mixture was extracted with dichloromethane. The organic layer was washed with saturated saline solution and dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was treated with diethyl ether, then, the precipitates were collected by filtration to give 410 mg (92%) of the title compound.

후처리

  1. stirringthe mixture was stirred for 2 hours at room temperature
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with saturated saline solution
  4. dry with materialdried over with anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. additionthe residue was treated with diethyl ether
  7. filtrationthe precipitates were collected by filtration

출처 및 근거

ORD 기록
ord-284bab2d2c0d428dac7a881f3fa0360d
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901315B2

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