Water → 2-bromo-N-methylbenzenesulfonamide

HRID 1665435Notes

Reaction equation

HRID 1665435 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[CH3:12][NH2:13].O>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:13][CH3:12])(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 5204032-Bromobenzenesulfonyl chloride

Product 1

HCID 8501412-bromo-N-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-Bromobenzenesulfonyl chloride (manufactured by Fluorochem Co., 25 g) was dissolved in tetrahydrofuran (40 mL), and under stirring at 0° C., 40% methylamine aqueous solution (TCI, 25 mL) was added dropwise thereto over ten minutes. After stirring the mixture at room temperature for 2 hours and 40 minutes, water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. To the residues, hexane and a small amount of ethyl acetate were added, followed by stirring. Solids were filtered to obtain the target compound (23.26 g).

Workup

  1. waitover ten minutes
  2. stirringAfter stirring the mixture at room temperature for 2 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. additionTo the residues, hexane and a small amount of ethyl acetate were added
  8. stirringby stirring
  9. filtrationSolids were filtered

Sources & evidence

ORD record
ord-bc88a6d7871c4a87b298a5bcc8f35e91
Source dataset
uspto-grants-2011_10
Patent number
US08039514B2

Reaction notes

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