Tetrahydrofuran → HCID 69690438, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9](=[C:12]2[CH2:16][CH2:15][CH2:14][NH:13]2)[C:10]#[N:11])=[CH:4][CH:3]=1.[H-].[Na+].[Cl:20][C:21]1C=CC=C[C:22]=1[C:23](Cl)=O.[CH2:30]1[CH2:34][O:33][CH2:32][CH2:31]1>>[Cl:20][C:21]1[CH:32]=[CH:31][C:30]([C:34]([N:13]2[CH2:14][CH2:15][CH2:16][C:12]2=[C:9]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[O:17])[C:10]#[N:11])=[O:33])=[CH:23][CH:22]=1Participants
Conditions
- Temperature
- 20 °C
Procedure
At 0° C., 1 g of the 3-(4-chlorophenyl)-3-oxo-2-pyrrolidin-2-ylidene-propionitrile prepared according to Example 1 is dissolved in 10 ml of THF and admixed with 0.3 g of NaH (60% pure), and the mixture is heated to 20° C. for two hours. 0.8 g of chlorobenzoyl chloride in 10 ml of THF is then added, and the mixture is stirred at room temperature for another 24 hours. The reaction mixture is then poured into ice-water and extracted with ethyl acetate, the extract is dried over magnesium sulphate and the solvent is evaporated under reduced pressure. The residue was chromatographed over silica gel using n-hexane/acetone 7:3. After evaporation of the solvent, one of the main fractions gave 0.2 g (yield 14% of theory) of 2-[1-(4-chlorobenzoyl)pyrrolidin-2-ylidene]-3-(4-chlorophenyl)-3-oxo-propionitrile of melting point 218° C.
Workup
- extractionextracted with ethyl acetate
- dry with materialthe extract is dried over magnesium sulphate
- customthe solvent is evaporated under reduced pressure
- customThe residue was chromatographed over silica gel
- customAfter evaporation of the solvent, one of the main fractions
Sources & evidence
- ORD record
- ord-377a1f46b1fd43769b0be038d097756d
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455472B1
Reaction notes
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