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Dichloromethane → 1-[4-(2-Bromoethoxy)phenyl]-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

HRID 723336
ノート
印刷プレビュー

反応式

HRID 723336 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][CH:14]=3)[C:9]2=[O:26])=[CH:4][CH:3]=1.[OH-].[Na+].ClCCl.[Br:32][CH2:33][CH2:34]Br>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Br:32][CH2:33][CH2:34][O:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[CH:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][CH:14]=3)[C:9]2=[O:26])=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 218734101-(4-Hydroxyphenyl)-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

生成物 1

HCID 120958581-[4-(2-Bromoethoxy)phenyl]-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

試薬・触媒・溶媒 1

HCID 94433
Tetrabutylammonium hydrogen sulfate
触媒

反応条件

温度
75 °C

実験手順

A solution of 1-(4-hydroxyphenyl)-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one (4.7 g) in 1,2-dibromoethane (23.6 ml) was mixed with sodium hydroxide solution (3N, 9.1 ml) and tetrabutylammonium hydrogen sulfate (232 mg). The mixture was heated at 75° C. for 2 hours. After cooling, the reaction mixture was mixed with dichloromethane and washed with sodium hydroxide solution (1N), hydrochloric acid (1N) and saturated brine. The organic phase was dried over magnesium sulfate and concentrated, and the residue was purified by chromatography on silica gel (eluent: dichloromethane/methanol 9:1). The product with the molecular weight of 451.32 (C23H19BrN2O3); MS (ESI): 451 ([M+H]+), was obtained in this way.

後処理

  1. temperatureAfter cooling
  2. washwashed with sodium hydroxide solution (1N), hydrochloric acid (1N) and saturated brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customthe residue was purified by chromatography on silica gel (eluent: dichloromethane/methanol 9:1)
  6. customMS (ESI): 451 ([M+H]+), was obtained in this way

出典と根拠

ORDレコード
ord-fe892cbda3e64447a214492c064e3981
出典データセット
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07141561B2

反応ノート

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