Pyridine → N-(4-bromo-2-ethylphenyl)methanesulfonamide

HRID 858604

Reaction equation

HRID 858604 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Br:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[C:9]([CH2:14][CH3:15])[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])=[C:9]([CH2:14][CH3:15])[CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 28012834-Bromo-2-ethylaniline

Product 1

HCID 6469152N-(4-bromo-2-ethylphenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methane sulfonyl chloride (1.93 ml, 0.025M) was added to a solution of 4-bromo-2-ethylaniline (5.0 g, 0.025M) and pyridine (2.02 ml, 0.025M) 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 clear oil (4.77 g).

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-203dffaafd3049e69236089ae16ed8d5
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Linked notes

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