Methyl iodide → HCID 15868664, compound

HRID 565171Notes

Reaction equation

HRID 565171 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([O:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14])[CH3:11])([O-:3])=[O:2].[H-].[Na+].[CH3:24]I>CN(C)C=O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([O:12][C:13]([N:15]([CH3:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14])[CH3:11])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15868663HCID 15868663, compound

Product 1

HCID 15868664HCID 15868664, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-[1-(2-Nitrophenyl)-1-ethoxycarbonyl]-N-phenylamine Ia (1.0 g; 3.4 mmol) in dry dimethylformamide (10 ml) was added to a slurry of sodium hydride (80% w/w; 0.19 g; 3.5 mmol) in dry dimethylformamide (20 ml) under an inert atmosphere. The mixture was stirred at room temperature for 15 min and then methyl iodide (2.1 ml; 34.9 mmol) was added over a period of 10 min. The reaction mixture was warmed to 50° C. and at this temperature for a further 30 min. The precipitate of sodium iodide was filtered off and the solvent was removed by evaporation under vacuum to give a viscous oil, which was purified by flash chromatography on silica, eluting with dichloromethane, to afford the required compound as a colourless solid. Recrystallization from toluene gave colourless crystals (0.9 g; 86% yield), mp 62-63° C.

Workup

  1. temperatureThe reaction mixture was warmed to 50° C. and at this temperature for a further 30 min
  2. filtrationThe precipitate of sodium iodide was filtered off
  3. customthe solvent was removed by evaporation under vacuum
  4. customto give a viscous oil, which
  5. customwas purified by flash chromatography on silica
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-663d901c82ef48838c1eed04ae351c8a
Source dataset
uspto-grants-2001_01
Patent number
US06171756B2

Reaction notes

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