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

HRID 558986노트

반응식

HRID 558986 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-561a477d4f9a4edda0dc30eb9b9c4675
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063038B2

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