Methyl iodide → N-(2-Methoxy-5-nitrobenzyl)acetamide

HRID 131668Notes

Reaction equation

HRID 131668 reaction equation
C(NCC1C=C([N+]([O-])=O)C=CC=1O)(=O)C.[CH3:16][O:17][C:18]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][C:19]=1[CH2:20][NH:21][C:22](=[O:24])[CH3:23].C(=O)([O-])[O-].[Na+].[Na+].IC>CC(C)=O>[CH3:16][O:17][C:18]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][C:19]=1[CH2:20][NH:21][C:22](=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 86760686HCID 86760686, compound

Product 1

HCID 20650534N-(2-Methoxy-5-nitrobenzyl)acetamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-(2-Methoxy-5-nitrobenzyl)acetamide 2-Acetamidomethyl-4-nitrophenol (2 g), sodium carbonate (2 g) and iodomethane (2 ml) were stirred in acetone (30 ml) at reflux 4 h. The mixture was filtered, the filtrate evaporated to dryness. The residue was warmed with aqueous sodium carbonate, washed with water and dried. Crystallised from ethanol/dilute acetic acid to give N-(2-methoxy-5-nitrobenzyl)acetamide as buff prisms. MP: 158.5-159.5° C.

Workup

  1. temperatureat reflux 4 h
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated to dryness
  4. temperatureThe residue was warmed with aqueous sodium carbonate
  5. washwashed with water
  6. customdried
  7. customCrystallised from ethanol/dilute acetic acid

Sources & evidence

ORD record
ord-90d9c20ccdbb45d28f3a8b946592ef38
Source dataset
uspto-grants-2008_06
Patent number
US07384963B2

Reaction notes

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