Pyridine → N-(3-bromophenyl)methanesulfonamide

HRID 531433Notes

Reaction equation

HRID 531433 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].N1C=CC=CC=1.[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(OCC)(=O)C>C(Cl)Cl.CCCCCC>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][S:16]([CH3:15])(=[O:18])=[O:17])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 115623-BromoanilineHCID 31297Methanesulfonyl chloride

Product 1

HCID 798932N-(3-bromophenyl)methanesulfonamideYield 96.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

To a stirred solution of 3-bromo aniline (6 g, 34.87 mmol) in dry DCM (200 ml) at 10° C. was added pyridine (4.13 mg, 52.31 mmol) followed by methane sulfonyl chloride (5.194 g, 45.34 mmol) and stirred at RT for 15 h. The reaction was monitored by TLC (35% Ethyl acetate in hexane). The reaction mixture was diluted with DCM (50 ml) and washed with 1N HCl (25 ml). The organic layer was dried over Na2SO4, and concentrated under reduced pressure to afford 8.45 g (96.3% yield) of N-(3-bromophenyl) methanesulfonamide. 1H NMR (DMSO-d6, 300 MHz): δ 10.01 (s, 1H), 7.368 (s, 1H), 7.365-7.19 (m, 3H), 3.03 (s, 1H). MS: m/z=251.8 (M+1).

Workup

  1. washwashed with 1N HCl (25 ml)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8148e6bdfe914bcba63514a808cd46ad
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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