4-Penten-2-one → HCID 19828702, compound
Reaction equation
Cl.[CH2:2]([C:4]1([C:13]2NC=N[CH:14]=2)[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)[CH3:3].CC(=[O:23])CC=C>>[CH:13]([C:4]1([C:2](=[O:23])[CH3:3])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)=[CH2:14]Participants
Procedure
EP 0247764 B (ORION-YHTYMÄ OY) Feb. 12, 1987 disclosed the following process for preparation of 5-(2-ethyl-2,3-dihydro-1H-inden-2-yl)-1H-imidazole hydrochloride. The process starts by reaction of alpha, alpha′-dibromo-o-xylene with 4-penten-2-one to obtain 1-(2,3-dihydro-2-vinyl-1H-inden-2-yl)ethanone. The obtained intermediate was brominated, e.g. with bromine, methylene chloride was used as solvent and 2-bromo-1-(2,3-dihydro-2-vinyl-1H-inden-2-yl)-ethanone was obtained, which is thereafter reacted with formamide in excess formamide to give a 4(5)-(2,3-dihydro-2-vinyl-1H-inden-2-ylimidazole hydrochloride. As the last step the vinyl group was catalytically hydrogenated to an ethyl group so as to form a product 4(5)-(2,3-dihydro-2-ethyl-1H-inden-2-yl) imidazole.
Sources & evidence
- ORD record
- ord-a67b31a6f02749a4bb75e6943b8fed8c
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431717B2
Reaction notes
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