Methyl iodide → HCID 12096250, compound

HRID 2185009Notes

Reaction equation

HRID 2185009 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:12]2[S:11](=[O:14])(=[O:13])[N:10]([CH2:15]CN(CC)CC)[CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.CI>O1CCCC1>[Br:3][C:4]1[C:12]2[S:11](=[O:14])(=[O:13])[N:10]([CH3:15])[CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12096239HCID 12096239, compound

Product 1

HCID 12096250HCID 12096250, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To sodium hydride (40 mg, 1.0 mmol) in tetrahydrofuran (10 mL) at 0° C. was added 7-bromo-N,N-diethyl-1,2-benzisothiazole-2(3H)-ethanamine 1,1-dioxide (0.26 g, 1.0 mmol). The reaction was stirred for 20 min and treated with methyl iodide (0.06 mL, 1.3 mmol). The resulting mixture was stirred at ambient temperature over 18 h, poured into ice water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude material was purified by a flush chromatography ((ethyl acetate/hexane, 1:4) to afford 7-bromo-2,3-dihydro-2-methyl-1,2-benzisothiazole 1,1-dioxide (0.15 g, 56%). LRMS (ES−): 262.0 (M−H)+.

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature over 18 h
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by a flush chromatography ((ethyl acetate/hexane, 1:4)

Sources & evidence

ORD record
ord-fa752c33032c4f1d9f30da1d8869b4a5
Source dataset
uspto-grants-2002_06
Patent number
US06399644B1

Reaction notes

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