Methyl iodide → 1-Methyl-1,3-dihydro-2H-2lambda~6~,1-benzothiazole-2,2-dione

HRID 899254Notes

Reaction equation

HRID 899254 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][S:2]1(=[O:11])=[O:10].CI.[C:14](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:14][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][S:2]1(=[O:10])=[O:11]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 155360091,3-Dihydro-2,1-benzisothiazole 2,2-dioxide

Product 1

HCID 126310511-Methyl-1,3-dihydro-2H-2lambda~6~,1-benzothiazole-2,2-dioneYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584019Toluene ethylacetateSolvent

Procedure

A mixture of 1,3-dihydro-2,1-benzisothiazole 2,2-dioxide (J. Heterocyclic Chem. 1986, 23, 1645., 401 mg, 2.37 mmol), methyl iodide (0.6 mL, 9.48 mmol) and potassium carbonate (328 mg, 2.37 mmol) in N,N-dimethylformamide (7 mL) was stirred for 4 h at room temperature. The reaction mixture was diluted with toluene/ethyl acetate (1/3), then washed with water for two times, and then the organic layer washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by preparative thin layer chromatography on silica gel developing with hexane/ethyl acetate (2/1) to afford 272 mg (63%) of the title compound as a slight brown syrup:

Workup

  1. washwashed with water for two times
  2. washthe organic layer washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified by preparative thin layer chromatography on silica gel developing with hexane/ethyl acetate (2/1)

Sources & evidence

ORD record
ord-5340db5fe02c4c7399bb46d1ae3114ec
Source dataset
uspto-grants-2008_04
Patent number
US07354925B2

Reaction notes

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