Sodium hydride → 1-[6-(4-Bromophenoxy)hexyl]-3-(4-fluorophenyl)-2-imidazolidinone

HRID 49264ノート

反応式

HRID 49264 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][NH:10][C:9]2=[O:13])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][CH:26]=1)C>CN(C)C=O>[Br:31][C:28]1[CH:29]=[CH:30][C:25]([O:24][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][N:10]2[CH2:11][CH2:12][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:9]2=[O:13])=[CH:26][CH:27]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 14807851-(4-Fluorophenyl)imidazolidin-2-oneHCID 20636597HCID 20636597、化合物

生成物 1

HCID 129864871-[6-(4-Bromophenoxy)hexyl]-3-(4-fluorophenyl)-2-imidazolidinone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-(4-fluorophenyl)-2-imidazolidinone (0.12 g, 0.65 mmol) dissolved in 10 mL dimethylformamide cooled in an ice bath was added NaH (60% dispersion in mineral oil, 39.0 mg, 0.98 mmol). The mixture was stirred at room temperature for 30 minutes and then cooled in ice bath. 1-Bromo-6-(4-bromophenoxy)heptane (0.22 g, 0.65 mmol) was added, and the mixture was stirred at room temperature for additional 4 hours. The reaction was quenched with methanol, and the solvents were removed under reduced pressure. 5 mL of saturated NH4Cl water solution and 10 mL of dichloromethane were added to the residue. The dichloromethane layer was dried over MgSO4, filtered, evaporated, and purified by column chromatography (ethyl acetate:MeOH=10:1) to give the product (i.e., Compound 7) as a white solid (0.14 g, 48%).

後処理

  1. temperaturecooled in an ice bath
  2. temperaturecooled in ice bath
  3. stirringthe mixture was stirred at room temperature for additional 4 hours
  4. customThe reaction was quenched with methanol
  5. customthe solvents were removed under reduced pressure
  6. addition5 mL of saturated NH4Cl water solution and 10 mL of dichloromethane were added to the residue
  7. dry with materialThe dichloromethane layer was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. custompurified by column chromatography (ethyl acetate:MeOH=10:1)

出典と根拠

ORDレコード
ord-7070ec48c1e54d5e9696f57c6b0256e5
出典データセット
uspto-grants-2004_03
特許番号
US06706739B2

反応ノート

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