Cesium carbonate → N-Methyl-N-(2-nitrophenyl)methanesulfonamide

HRID 1487236Notes

Reaction equation

HRID 1487236 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][NH:8][S:9]([CH3:12])(=[O:11])=[O:10].F[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21]>C(#N)C>[CH3:7][N:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21])[S:9]([CH3:12])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 97632N-Methylmethanesulfonamide

Product 1

HCID 13314625N-Methyl-N-(2-nitrophenyl)methanesulfonamideYield 56.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of cesium carbonate (20.2 g, 0.065 mol) in acetonitrile (500 mL) at room temperature was added N-methylmethanesulfonamide (5.33 g, 0.049 mol) and 1-fluoro-2-nitrobenzene (4.59 g, 0.033 mol) dropwise over 10-15 minutes. The reaction was stirred at room temperature for 12 hours. Upon completion, the mixture was filtered and then concentrated. The residue was purified by silica gel chromatography (dichloromethane) to afford the product N-methyl-N-(2-nitrophenyl)methanesulfonamide (4.2 g, yield 56.1%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.92-7.94 (dd, 1H, J=1.2 Hz, 8.0 Hz), 7.74-7.81 (m, 2H), 7.57-7.62 (m, 1H), 3.27 (s, 3H), 3.03 (s, 3H).

Workup

  1. filtrationUpon completion, the mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (dichloromethane)

Sources & evidence

ORD record
ord-f2299ccb4175488eabe21ecd321f8b2d
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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