Methyl iodide → 1,2-Benzisothiazole, 5-bromo-2,3-dihydro-2-methyl-, 1,1-dioxide

HRID 1846026Notes

Reaction equation

HRID 1846026 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9](=[O:11])(=[O:10])[NH:8][CH2:7][C:6]=2[CH:12]=1.[C:13](=O)([O-])[O-].[K+].[K+].IC>CCO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9](=[O:10])(=[O:11])[N:8]([CH3:13])[CH2:7][C:6]=2[CH:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 706549535-bromo-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide

Product 1

HCID 684304291,2-Benzisothiazole, 5-bromo-2,3-dihydro-2-methyl-, 1,1-dioxideYield 725.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-bromo-2,3-dihydro-1,2-benzisothiazole 1,1-dioxide (200 mg, 0.92 mmol) and potassium carbonate (128 mg, 0.92 mmol) in EtOH (2 mL) was added iodomethane (0.2 mL, 3.2 mmol) and the reaction was stirred at room temperature for 18 hours followed by heating to 50° C. for 2 hours. The reaction was cooled, concentrated in vacuo and diluted with DCM (20 mL). The solution was washed with water (20 mL), dried over Na2SO4 and concentrated in vacuo to afford the title compound as a white solid (1.75 g, 83%).

Workup

  1. temperatureby heating to 50° C. for 2 hours
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated in vacuo
  4. additiondiluted with DCM (20 mL)
  5. washThe solution was washed with water (20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1ff30b7a5e5470ebe35bfaa3d5b588c
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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