Acetic Acid → 2,2'-[5-(5-Formylimidazol-1-yl)-1,3-phenylene]di(2-methylpropiononitrile)
Reaction equation
[CH:1]([C:3]1[N:4]=[CH:5][N:6](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:7]=1)=[O:2].BrC[C:29]1[CH:30]=[C:31]([C:40]([CH3:44])([CH3:43])[C:41]#[N:42])[CH:32]=[C:33]([C:35]([CH3:39])([CH3:38])[C:36]#[N:37])[CH:34]=1.C(#N)C.C(O)(=O)C>O>[CH:1]([C:3]1[N:4]([C:29]2[CH:34]=[C:33]([C:35]([CH3:38])([CH3:39])[C:36]#[N:37])[CH:32]=[C:31]([C:40]([CH3:43])([CH3:44])[C:41]#[N:42])[CH:30]=2)[CH:5]=[N:6][CH:7]=1)=[O:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 4-formyl-1-tritylimidazole (0.5 g), 2,2'-(5-bromomethyl-1,3-phenylene)di(2-methylpropiononitrile) and acetonitrile (2 ml) was heated under reflux for 30 h. The reaction mixture was treated with acetic acid (8 ml) and water (2 ml) and the mixture was then heated at 90° for 1 h. The mixture was diluted with water (20 ml) and washed with ether, the aqueous phase was basified with sodium carbonate, and the mixture was extracted three times with ethyl acetate. The combined extracts were dried and evaporated to dryness, and the residue was purified by flash chromatography using methanol (2% by volume) in chloroform as eluant, to give 2,2'-[5-(5-formylimidazol-1-yl)-1,3-phenylene]di(2-methylpropiononitrile), mp 108°-111°.
Workup
- temperaturewas heated
- temperatureunder reflux for 30 h
- temperaturethe mixture was then heated at 90° for 1 h
- washwashed with ether
- extractionthe mixture was extracted three times with ethyl acetate
- customThe combined extracts were dried
- customevaporated to dryness
- customthe residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-0556d3de971f4cc28e9e282b3275bd59
- Source dataset
- uspto-grants-1990_06
- Patent number
- US04935437
Reaction notes
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