Methyl iodide → N-[(4-Methoxyphenyl)methyl]-N-methylacetamide

HRID 392829Notes

Reaction equation

HRID 392829 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:15]=[CH:14][C:8]([CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:7][CH:6]=1.I[CH3:17]>>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]([CH3:17])[C:11](=[O:13])[CH3:12])=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 37050N-((4-methoxyphenyl)methyl)acetamide

Product 1

HCID 22660871N-[(4-Methoxyphenyl)methyl]-N-methylacetamideYield 90%

Procedure

Sodium hydride (60% in mineral oil) (1.11 grams, 27.4 mmol) was measured into a round bottom flask and triturated with hexanes. To this was added pure N-(4-methoxybenzyl)-acetamide (1.23 grams, 6.9 mmol) followed by iodomethane (1.95 grams, 13.7 mmol)and the resulting mixture stirred overnight. The reaction was filtered and the solvent removed under vacuum. The crude product was purified by flash column chromatography (SiO2, 2% EtOH in methylene chloride) to yield 1.2 grams of a colorless oil. HRMS (M+H) calcd for C11H16NO2: 194.1181; found: 194.1177. 1H NMR and 13C NMR show a mixture of rotamers at room temperature. 1H NMR (500 MHz, CDCl3) δ: 2.13 (s), 2.15 (s), 2.89 (s), 2.90 (s), 3.78 (s), 3.80 (s), 4.45 (s), 4.50 (s), 6.86 (m), 7.08 (d, J=9), 7.17 (d, J=9). 13C NMR (125 MHz, CDCl3) δ: 21.50, 21.91, 33.49, 35.33, 49.95, 53.72, 55.28, 113.95, 114.32, 127.66, 128.46, 129.44, 129.52, 158.95, 159.13, 170.63, 170.91.

Workup

  1. customtriturated with hexanes
  2. filtrationThe reaction was filtered
  3. customthe solvent removed under vacuum
  4. customThe crude product was purified by flash column chromatography (SiO2, 2% EtOH in methylene chloride)

Sources & evidence

ORD record
ord-f49d127dfcd64445986e6643366d27a0
Source dataset
uspto-grants-2004_10
Patent number
US06803378B2

Reaction notes

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