Ethanol → HCID 178418803, 화합물

HRID 10728

반응식

HRID 10728 반응식
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7](OC)[CH:6]=1)=O.[CH:15]1([C:18]([NH2:20])=[NH:19])[CH2:17][CH2:16]1.[OH-].[Na+].[CH2:23]([OH:25])C>>[CH:15]1([C:18]2[NH:19][CH:2]=[C:3]([C:5]3[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[CH:9][C:10]=3[O:25][CH3:23])[N:20]=2)[CH2:17][CH2:16]1

참가 물질

5

반응물 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 2704232-Bromo-1-(3,4-dimethoxyphenyl)ethan-1-oneHCID 431751Cyclopropanecarboximidamide

생성물 1

HCID 178418803HCID 178418803, 화합물

실험 절차

Ex-105A: A solution of 2-bromo-1-(3,4-dimethoxy-phenyl)-ethanone (0.3 g, 1.16 mmol), cyclopropanecarboxamidine (0.14 g, 1.16 mmol) and sodium hydroxide (0.18 g, 4.5 mmol) in ethanol was refluxed overnight. The solvent was removed under reduced pressure, the residue taken up to water. The aqueous solution was then extracted with dichloromethane which was subsequently washed with brine, dried over sodium bicarbonate and concentrated. The crude product was purified by flash chromatography. Elution with ethyl acetate (50%, v/v, in hexane) then methanol (10%, v/v in dichloromethane) afforded 2-cyclopropyl-4-(2,4-dimethoxy-phenyl)-1H-imidazole as white solid (0.1 5 g, 53%): 1HNMR (CDCl3) δ 9.50 (bs, 1H), 7.63 (s, 1H), 7.20 (s, 1H), 6.57–6.53 (m, 2H), 3.93 (s, 3H), 3.03 (s, 3H), 1.97–1.93 (m, 1H), 1.00–0.94 (m, 4H). MS m/z=245 ([M+H]+, 100%).

후처리

  1. customThe solvent was removed under reduced pressure
  2. extractionThe aqueous solution was then extracted with dichloromethane which
  3. washwas subsequently washed with brine
  4. dry with materialdried over sodium bicarbonate
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography
  7. washElution with ethyl acetate (50%, v/v, in hexane)

출처 및 근거

ORD 기록
ord-bbb2cd7fd873464ea1dfd997d79efdb3
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094801B2

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