Dimethyl Sulfate → 3-fluoro-N-methyl-5-nitrobenzamide

HRID 522913Notes

Reaction equation

HRID 522913 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([NH2:7])=[O:6].[C:14](=O)([O-])[O-].[Cs+].[Cs+].S(OC)(OC)(=O)=O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([NH:7][CH3:14])=[O:6]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 10796Cesium carbonateHCID 509984493-Fluoro-5-nitrobenzamide

Product 1

HCID 594427293-fluoro-N-methyl-5-nitrobenzamideYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-fluoro-5-nitrobenzamide (1.0 g, 5.43 mmoL) in DMF (17 mL) was added cesium carbonate (2.6 g, 8.14 mmoL) and dimethyl sulphate (547 mg, 4.34 mmol) and the reaction mixture was stirred at RT for 24 h. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×40 ml). The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 3-fluoro-N-methyl-5-nitrobenzamide (0.800 g, 80%) as a solid. Observed mass (M−1): 196.9.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc (2×40 ml)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-9c024b6c0bdc419e8090b4c52da45f4b
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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