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

HRID 49264노트

반응식

HRID 49264 반응식
[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

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 14807851-(4-Fluorophenyl)imidazolidin-2-oneHCID 20636597HCID 20636597, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-7070ec48c1e54d5e9696f57c6b0256e5
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706739B2

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