Ethanol → HCID 178418803、化合物

HRID 10728

反応式

HRID 10728 の反応式
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

参加物

5

反応物 4

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

生成物 1

HCID 178418803HCID 178418803、化合物

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-bbb2cd7fd873464ea1dfd997d79efdb3
出典データセット
uspto-grants-2006_08
特許番号
US07094801B2

関連ノート

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