Sodium Iodide → N-(4-bromo-2-chloro-phenyl)-2-{4-[4-(2-hydroxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide

HRID 1433749노트

반응식

HRID 1433749 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:40])[CH:10]([N:19]2[C:23](=[O:24])[CH:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][O:34]C(C)(C)C)=[CH:27][CH:26]=3)[NH:21][C:20]2=[O:39])[CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])=[C:4]([Cl:41])[CH:3]=1.C(#N)C.C[Si](Cl)(C)C.[I-].[Na+]>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:40])[CH:10]([N:19]2[C:23](=[O:24])[CH:22]([C:25]3[CH:26]=[CH:27][C:28]([O:31][CH2:32][CH2:33][OH:34])=[CH:29][CH:30]=3)[NH:21][C:20]2=[O:39])[CH:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH3:12])=[C:4]([Cl:41])[CH:3]=1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 68619472N-(4-Bromo-2-chloro-phenyl)-2-{4-[4-(2-tert-butoxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide

생성물 1

HCID 68620084N-(4-bromo-2-chloro-phenyl)-2-{4-[4-(2-hydroxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide수율 76.7%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

N-(4-Bromo-2-chloro-phenyl)-2-{4-[4-(2-tert-butoxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide (300 mg) was dissolved in dichloromethane (2 mL) and acetonitrile (2 mL) in an ice bath. Trimethylsilyl chloride (0.36 mL, 2.8 mmol) was added followed by sodium iodide (352 mg, 2.35 mmol). The mixture was stirred at 0° C. for 1.5 hours and then diluted with ethyl acetate. The mixture was washed with aqueous sodium bisulfite, washed with brine, dried over sodium sulfate and concentrated in vacuo. Trituration of the residue with hexanes gave N-(4-bromo-2-chloro-phenyl)-2-{4-[4-(2-hydroxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide (210 mg, 76%).

후처리

  1. washThe mixture was washed with aqueous sodium bisulfite
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7ce8120c416e4078acad6492d32fd3ba
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612212B2

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