Methyl iodide → N-(2-Bromophenyl)-N-methylmethanesulfonamide

HRID 472492Notes

Reaction equation

HRID 472492 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[C:13](=O)([O-])[O-].[Cs+].[Cs+].IC>C(#N)C.ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 3629878N-(2-bromophenyl)methanesulfonamide

Product 1

HCID 67478926N-(2-Bromophenyl)-N-methylmethanesulfonamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

196 b) To a suspension of N-(2-bromo-phenyl)-methanesulfonamide (5.01 g, 20.0 mmol) and cesium carbonate (7.2 g, 22 mmol) in acetonitrile (20 mL) was added iodomethane (1.4 mL, 22 mmol). The mixture was stirred at room temperature for 24 hours then diluted with dichloromethane (30 mL), filtered through a plug of diatomaceous earth and evaporated. N-(2-Bromo-phenyl)-N-methyl-methanesulfonamide was isolated as a pale orange solid (5.22 g, 98%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.65 (d, J=8.0 Hz, 1H), 7.50 (d, J=7.9 Hz, 1H), 7.37 (t, J=7.4 Hz, 1H), 7.23 (t, J=8.2 Hz, 1H), 3.29 (s, 3H), 3.06 (s, 3H). MS=286, 288 (MH)+.

Workup

  1. filtrationfiltered through a plug of diatomaceous earth
  2. customevaporated

Sources & evidence

ORD record
ord-4f56eed96f984dc5a0a47097350a924f
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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