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 1433749ノート

反応式

HRID 1433749 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-7ce8120c416e4078acad6492d32fd3ba
出典データセット
uspto-grants-2009_11
特許番号
US07612212B2

反応ノート

読み込み中…