Water → 1-(Methylsulfonyl)-5-nitroindoline

HRID 1398069Notes

Reaction equation

HRID 1398069 reaction equation
[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]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 362195-Nitroindoline

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-284bab2d2c0d428dac7a881f3fa0360d
Source dataset
uspto-grants-2014_12
Patent number
US08901315B2

Reaction notes

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