Methyl iodide → 4-cyano-N-(2-furan-2-ylphenyl)-3,N-dimethylbenzamide

HRID 558986ノート

反応式

HRID 558986 の反応式
[C:1]([C:3]1[CH:22]=[CH:21][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)=[O:8])=[CH:5][C:4]=1[CH3:23])#[N:2].[H-].[Na+].I[CH3:27]>CN(C=O)C>[C:1]([C:3]1[CH:22]=[CH:21][C:6]([C:7]([N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)[CH3:27])=[O:8])=[CH:5][C:4]=1[CH3:23])#[N:2]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 574707854-Cyano-N-(2-furan-2-ylphenyl)-3-methylbenzamide

生成物 1

HCID 574707864-cyano-N-(2-furan-2-ylphenyl)-3,N-dimethylbenzamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-cyano-N-(2-furan-2-ylphenyl)-3-methylbenzamide from Example 21B (222 mg, 0.734 mmol) in DMF (8.0 ml) was added sodium hydride (60%, 44 mg, 1.10 mmol) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 45 min. Iodomethane (68 μl, 1.10 mmol) was added and the mixture was stirred for 18 h. The mixture was evaporated in vacuo and the residue was taken up in EtOAc, washed with brine, dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant pet.ether:EtOAc 80:20) to give a brown solid; yield 198 mg, 85%.

後処理

  1. temperaturewhile cooling in an ice/water bath
  2. stirringthe mixture was stirred for 18 h
  3. customThe mixture was evaporated in vacuo
  4. washwashed with brine
  5. customdried
  6. customevaporated in vacuo
  7. customThe residue was purified by flash chromatography on silica (eluant pet.ether:EtOAc 80:20)
  8. customto give a brown solid

出典と根拠

ORDレコード
ord-561a477d4f9a4edda0dc30eb9b9c4675
出典データセット
uspto-grants-2011_11
特許番号
US08063038B2

反応ノート

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