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

HRID 392829ノート

反応式

HRID 392829 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f49d127dfcd64445986e6643366d27a0
出典データセット
uspto-grants-2004_10
特許番号
US06803378B2

反応ノート

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