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

HRID 723336
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인쇄 미리보기

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HRID 723336 반응식
[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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 94433
Tetrabutylammonium hydrogen sulfate
촉매

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온도
75 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fe892cbda3e64447a214492c064e3981
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07141561B2

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