Hydrochloric Acid → 1-(9H-fluoren-2-yl)-2-(2-methyl-1H-imidazol-1-yl)ethanone hydrochloride
Reaction equation
Br[CH2:2][C:3]([C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][C:7]=2[CH:6]=1)=[O:4].[CH3:18][C:19]1[NH:20][CH:21]=[CH:22][N:23]=1.O.[OH-].[Na+].[ClH:27]>C(OCC)C.CN(C)C=O>[ClH:27].[CH:6]1[C:7]2[CH2:8][C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15]=2[CH:16]=[CH:17][C:5]=1[C:3](=[O:4])[CH2:2][N:20]1[CH:21]=[CH:22][N:23]=[C:19]1[CH3:18]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 12.0 g. of 2-(bromoacetyl)fluorene in 150 ml. of dimethylformamide was added to an ice-cooled solution of 24 g. of 2-methylimidazole in 150 ml. of dimethylformamide. The mixture was allowed to warm to room temperature and was stirred overnight. The reaction mixture was poured into water containing one equivalent of sodium hydroxide. The resulting precipitate was filtered and the filtrate was extracted with ethyl acetate. The ethyl acetate solution was washed first with water and then with a saturated sodium chloride solution, dried over sodium sulfate, filtered, and evaporated in vacuo. The residue was combined with the filtered precipitate and dissolved in hot acetone. Three equivalents of hydrochloric acid were added and upon the addition of diethyl ether, 6.65 g. of the desired title product formed which were recovered by filtration, m.p. 275°-276° C. with decomposition.
Workup
- temperaturecooled solution of 24 g
- filtrationThe resulting precipitate was filtered
- extractionthe filtrate was extracted with ethyl acetate
- washThe ethyl acetate solution was washed first with water
- dry with materialwith a saturated sodium chloride solution, dried over sodium sulfate
- filtrationfiltered
- customevaporated in vacuo
- dissolutiondissolved in hot acetone
Sources & evidence
- ORD record
- ord-3f2542a7bfe4467db6b6f95d240dafe2
- Source dataset
- uspto-grants-1985_08
- Patent number
- US04533670
Reaction notes
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