Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][O:10]C.[N+:12]([C:15]1[O:21][C:18]([CH2:19]O)=[CH:17][CH:16]=1)([O-:14])=[O:13]>C1C=CC=CC=1.C(OCC)C.FB(F)F>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[CH:19][C:18]1[O:21][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=1)[CH:9]=[O:10]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
4.0 g of 1-(2-chlorophenyl)-2-methoxyethylene are added dropwise within 20 minutes to 9.55 g of 5-nitrofurfurol in 12 cc of dry benzene at room temperature after the addition of one drop of diethyl ether/trifluoroborane. The mixture is stirred at 35°-40° for 1 hour and is then successively washed with a 5% aqueous sodium acetate solution and water, the benzene solution is dried over magnesium sulphate and concentrated by evaporation. The residue is taken up in 3 cc of concentrated hydrochloric acid, 17 cc of water and 120 cc of glacial acetic acid, and the mixture is stirred at 80°-85° for 3 hours. The mixture is concentrated in a vacuum, and, after cooling, the title compound is obtained as yellow crystals having a M.P. of 148°-151°.
Workup
- washis then successively washed with a 5% aqueous sodium acetate solution and water
- dry with materialthe benzene solution is dried over magnesium sulphate
- concentrationconcentrated by evaporation
- stirring17 cc of water and 120 cc of glacial acetic acid, and the mixture is stirred at 80°-85° for 3 hours
- concentrationThe mixture is concentrated in a vacuum
- temperatureafter cooling
Sources & evidence
- ORD record
- ord-58b789c282864d8eb44613f4516d772f
- Source dataset
- uspto-grants-1976_09
- Patent number
- US03982007
Linked notes
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