Pyridine → N-(4-Bromophenyl)methanesulfonamide

HRID 1453054Notes

Reaction equation

HRID 1453054 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Br:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1.N1C=CC=CC=1>ClCCl>[Br:6][C:7]1[CH:13]=[CH:12][C:10]([NH:11][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 78074-BromoanilineHCID 31297Methanesulfonyl chloride

Product 1

HCID 706841N-(4-Bromophenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methane sulfonyl chloride (2.4 ml, 0.031M) was added to a solution of 4-bromo-aniline (5.28 g, 0.031M) and pyridine (2.5 ml, 0.031M) in dichloromethane (100 ml) at 0° C. The reaction mixture was stirred for 1 hr, after which time it was partitioned between dichloromethane (100 ml) and 1N hydrochloric acid (100 ml). The organics were separated and dried over magnesium sulfate, filtered and concentrated in vacuuo to afford the title compound as a white solid (6.37 g). 1H NMR (CDCl3): 2.97 (s, 3H), 6.81 (d, J=2.56 Hz, 2H), 7.25 (d, J=2.56 Hz, 2H),).

Workup

  1. customafter which time it was partitioned between dichloromethane (100 ml) and 1N hydrochloric acid (100 ml)
  2. customThe organics were separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuuo

Sources & evidence

ORD record
ord-1a39a56e69604c0f88656bbcd2c5d03d
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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