Methyl iodide → HCID 86697165, compound

HRID 237504Notes

Reaction equation

HRID 237504 reaction equation
[Br:1][C:2]1[C:16]([CH3:17])=[CH:15][C:5]([O:6][CH:7]2[CH2:12][CH2:11][S:10](=[O:14])(=[O:13])[NH:9][CH2:8]2)=[CH:4][C:3]=1[CH3:18].[H-].[Na+].I[CH3:22]>CN(C)C=O>[Br:1][C:2]1[C:16]([CH3:17])=[CH:15][C:5]([O:6][CH:7]2[CH2:12][CH2:11][S:10](=[O:14])(=[O:13])[N:9]([CH3:22])[CH2:8]2)=[CH:4][C:3]=1[CH3:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86697164HCID 86697164, compound

Product 1

HCID 86697165HCID 86697165, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-Bromo-3,5-dimethyl-phenoxy)-[1,2]thiazinane 1,1-dioxide (110 mg) and sodium hydride (14.5 mg of a 60% mineral oil suspension) are suspended in 2 mL of N,N-dimethylformamide. Iodomethane (0.02 mL) is added and the reaction mixture is stirred at room temperature for 3 h. The solvent is removed, water is added and the reaction mixture is extracted with ethyl acetate. The organic phase is separated, dried over sodium sulfate and concentrated under vacuum. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→60:40) to give the title compound. Yield: 110 mg.

Workup

  1. customThe solvent is removed
  2. additionwater is added
  3. extractionthe reaction mixture is extracted with ethyl acetate
  4. customThe organic phase is separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→60:40)

Sources & evidence

ORD record
ord-6aace1c8ca824b5db097155c623a8aef
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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