Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → N-(3-formylphenyl)acetamide

HRID 852881ノート

反応式

HRID 852881 の反応式
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:15])[CH3:14])[CH:9]=[CH:10][CH:11]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O.O>[CH:2]([C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:15])[CH3:14])[CH:9]=[CH:10][CH:11]=1)=[O:1]

参加物

4

反応物 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 13987600N-[3-(1,3-dioxolan-2-yl)phenyl]acetamide

生成物 1

HCID 256849N-(3-formylphenyl)acetamide収率 99%

試薬・触媒・溶媒 1

HCID 18366337Propan-2-one--water (1/1)溶媒

実験手順

A mixture of N-(3-[1,3]Dioxolan-2-yl-phenyl)-acetamide (7.8 g, 0.037 mol) and pyridinium-p-toluenesulfonate (2.8 g, 0.011 mol) in acetone-water (4:1, 400 mL) was refluxed for 1 hr. The solution was then cooled to room temperature, and the bulk of the solvent (˜90%) removed under reduced pressure. The remaining solution was then extracted with EtOAc, and the combined extracts washed with saturated NaHCO3, brine, and dried with MgSO4. Evaporation of the solvent gave N-(3-Formyl-phenyl)-acetamide (5.98 g, 98%) as an orange oil. 1H NMR (CDCl3) δ 2.22 (s, 3H), 7.46 (t, J=8 Hz, 1H), 7.59 (d, J=8 Hz, 1H), 7.89 (d, J=8 Hz, 1H), 8.07 (s, 1H), 8.69 (br s, 1H), 9.94 (s, 1H). 13C NMR (CDCl3) δ 193.9, 171.0, 140.8, 138.5, 131.2, 127.5, 127.1, 122.0, 26.0.

後処理

  1. temperaturewas refluxed for 1 hr
  2. customthe bulk of the solvent (˜90%) removed under reduced pressure
  3. extractionThe remaining solution was then extracted with EtOAc
  4. washthe combined extracts washed with saturated NaHCO3, brine
  5. dry with materialdried with MgSO4
  6. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-ee0052e72b4449dd90637151a0802cf1
出典データセット
uspto-grants-2007_08
特許番号
US07253194B2

反応ノート

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