Water → 4-bromo-N-(tert-butyl)-N-methylbenzenesulfonamide

HRID 509275Notes

Reaction equation

HRID 509275 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N-:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:16](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:16])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86692076HCID 86692076, compound

Product 1

HCID 579800364-bromo-N-(tert-butyl)-N-methylbenzenesulfonamideYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-N-(tert-butyl)benzenesulfonyl amide (100 mg, 0.342 mmol) and potassium carbonate (95 mg, 0.684 mmol) were dissolved in DMF (2 ml), followed by addition of iodomethane (0.043 ml, 0.684 mmol), and then the resulting liquid was stirred at room temperature for 18 hours. Distilled water (10 ml) was added to the resulting reaction liquid, followed by extraction with EtOAc (10 ml×3). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (20% EtOAc/Hexanes), to obtain 77 mg of yellow oil (73%).

Workup

  1. extractionfollowed by extraction with EtOAc (10 ml×3)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfollowed by filtration and concentration
  4. customthe residue thus obtained

Sources & evidence

ORD record
ord-2f6b9d077082469ba371acb8bf6a6e8f
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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