Ethanol → HCID 178418803, compound

HRID 10728Notes

Reaction equation

HRID 10728 reaction equation
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

Participants

5

Reactant 4

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

Product 1

HCID 178418803HCID 178418803, compound

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-bbb2cd7fd873464ea1dfd997d79efdb3
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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