3-Bromoaniline → N-(3-bromophenyl)methanesulfonamide

HRID 1978029Notes

Reaction equation

HRID 1978029 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH3:9][S:10](Cl)(=[O:12])=[O:11]>N1C=CC=CC=1>[CH3:9][S:10]([NH:5][C:4]1[CH:3]=[C:2]([Br:1])[CH:8]=[CH:7][CH:6]=1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 31297Methanesulfonyl chloride

Product 1

HCID 798932N-(3-bromophenyl)methanesulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

The m-bromo aniline was dissolved in 40 mL of pyridine and cooled to 0° C. followed by addition of methansulfonyl chloride dropwise via syringe. After 10 minutes, the solution was warmed to room temperature and stirred for 4 hours. Upon concentration the residue was partitioned between 350 mL of H2O and 500 mL of dichloromethane in a separatory funnel. The organics were separated and washed with 100 mL of 3N HCl, 200 mL of sat'd NaHCO3 and dried over MgSO4. Upon filtration and concentration in vacuo an off-white solid was obtained. This product was recrystallized from dichloromethane/hexanes to afford 6.7 g (90%) of the desired product as white needles.

Workup

  1. temperaturethe solution was warmed to room temperature
  2. concentrationUpon concentration the residue
  3. customwas partitioned between 350 mL of H2O and 500 mL of dichloromethane in a separatory funnel
  4. customThe organics were separated
  5. washwashed with 100 mL of 3N HCl, 200 mL of sat'd NaHCO3
  6. dry with materialdried over MgSO4
  7. filtrationUpon filtration and concentration in vacuo an off-white solid
  8. customwas obtained
  9. customThis product was recrystallized from dichloromethane/hexanes

Sources & evidence

ORD record
ord-320385bc75d248379b793bec49df0f9e
Source dataset
uspto-grants-2001_05
Patent number
US06235786B1

Reaction notes

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