Sodium hydride → 1-(4-Chlorophenyl)-3-(5-[3-(4-methoxyphenoxy)propoxy]pentyl)-2-imidazolidinone

HRID 49263ノート

反応式

HRID 49263 の反応式
[Cl: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][O:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][CH2:11][N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH2:25][O:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[C:9]2=[O:13])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 264512-Imidazolidinone, 1-(p-chlorophenyl)-HCID 20636584HCID 20636584、化合物

生成物 1

HCID 129864861-(4-Chlorophenyl)-3-(5-[3-(4-methoxyphenoxy)propoxy]pentyl)-2-imidazolidinone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-(4-chlorophenyl)-2-imidazolidinone (0.10 g, 0.53 mmol) dissolved in 10 mL dimethylformamide cooled in an ice bath was added NaH (60% dispersion in mineral oil, 27.3 mg, 0.80 mmol). The mixture was stirred at room temperature for 30 min and then cooled in ice bath. 1-{3-[(5-Bromopentyl)oxy]propoxy}-4-methoxybenzene (0.18 g, 0.53 mmol) was added, and the mixture was stirred at room temperature for additional 4 hours. The reaction was quenched with MeOH, and the solvents were pumped off. 5 mL saturated aqueous NH4Cl solution and 10 mL dichloromethane were successively added to the residue. The dichloromethane layer was separated and dried over MgSO4, filtered, evaporated, and purified by column chromatography (ethyl acetate:MeOH=10:1) to give the product (i.e., Compound 6) as a white solid (0.16 g, 68%).

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 MeOH
  5. addition5 mL saturated aqueous NH4Cl solution and 10 mL dichloromethane were successively added to the residue
  6. customThe dichloromethane layer was separated
  7. dry with materialdried 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-9a4491e1858b469db7faea809a060b80
出典データセット
uspto-grants-2004_03
特許番号
US06706739B2

反応ノート

読み込み中…