Methyl iodide → Cyclohexyl-n-(3-fluoro-4-nitrophenyl)-n-methyl-carboxamide

HRID 722413Notes

Reaction equation

HRID 722413 reaction equation
[H-].[Na+].[CH:3]1([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([F:21])[CH:13]=2)=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:22]I>CN(C=O)C>[CH:3]1([C:9]([N:11]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([F:21])[CH:13]=2)[CH3:22])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58742600Cyclohexyl-n-(3-fluoro-4-nitrophenyl)carboxamide

Product 1

HCID 58742757Cyclohexyl-n-(3-fluoro-4-nitrophenyl)-n-methyl-carboxamideYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% Sodium hydride powder (1.1 mmol, 0.045 g) was added in portions to a cooled solution of cyclohexyl-N-(3-fluoro-4-nitrophenyl)carboxamide (1 mmol, 0.266 g) and methyl iodide (1.2 mmol, 0.16 g) in DMF (5 mL). The reaction mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure and the residue was dissolved in CH2Cl2 (50 mL) and washed with 10% NaHCO3, brine, H2O, dried over Na2SO4 and the solvent evaporated to afford 0.23 g of the title compound as a yellow oily residue (Yield: 82%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in CH2Cl2 (50 mL)
  3. washwashed with 10% NaHCO3, brine, H2O
  4. dry with materialdried over Na2SO4
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-21e150ba13084f9f9f8771e7a3f4eb73
Source dataset
uspto-grants-2006_11
Patent number
US07138420B2

Reaction notes

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