Methylamine → 4-bromo-N-methylbenzene-1-sulfonamide

HRID 2239382Notes

Reaction equation

HRID 2239382 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][NH2:13]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:13][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 7396p-Bromobenzenesulfonyl chloride

Product 1

HCID 1012154-bromo-N-methylbenzene-1-sulfonamideYield 28%

Procedure

4-Bromobenzene sulfonyl chloride (0.40 g, 1.56 mmol) and methylamine (10 mL, 33% in ethanol) were stirred in a sealed tube for 16 hours. The reaction mixture was concentrated in vacuo onto the Celite® reagent. The crude product was purified via Isco chromatography (the Redisep™ column, silica, gradient 0-3% ethyl acetate-dichloromethane) to provide 4-bromo-N-methylbenzenesulfonamide (0.11 g, 28%). MS (ESI) m/z 250. High performance liquid chromatography (HPLC) purity 100.0% at 210-370 nm, 7.4 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/Acetonitrile (ACN)+MeOH) for 10 min., hold 4 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo onto the Celite® reagent
  2. customThe crude product was purified via Isco chromatography (the Redisep™ column, silica, gradient 0-3% ethyl acetate-dichloromethane)

Sources & evidence

ORD record
ord-ec2485406c2445ffb0398b5f328799bd
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

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