Methyl iodide → HCID 22119915, compound

HRID 1274655Notes

Reaction equation

HRID 1274655 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])[C:17]=3[CH:26]=2)[C:3]1=[O:27].[H-].[Na+].I[CH3:31]>O1CCCC1>[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH:21]([S:22]([CH3:25])(=[O:24])=[O:23])[CH3:31])[C:17]=3[CH:26]=2)[C:3]1=[O:27]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22119920HCID 22119920, compound

Product 1

HCID 22119915HCID 22119915, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1-methyl-3-{3-[(methylsulfonyl)methyl]-1,2-benzisothiazol-5-yl}-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (1.00 g, 0.00238 mol) in tetrahydrofuran is added sodium hydride (60%, 0.120 g, 0.00300 mol). The resultant mixture is stirred one hour at room temperature and treated with iodomethane (0.220 ml, 0.00360 mol). The mixture is stirred two hours at room temperature, partially concentrated in vacuo, diluted with water, and extracted with ethyl acetate. The organic layer is washed with water, filtered through anhydrous magnesium sulfate and concentrated in vacuo to a brown foam. The foam is chromatographed on silica gel with methylene chloride/ether to give the title compound as an off-white solid (0.420 g, 40.4%) which is identified by NMR spectral analysis.

Workup

  1. concentrationpartially concentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. filtrationfiltered through anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo to a brown foam
  7. customThe foam is chromatographed on silica gel with methylene chloride/ether

Sources & evidence

ORD record
ord-7f6e8a50738448c8a6dd9167a20f8307
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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