Acetic Acid → 4-(2-Cyano-3-oxobut-1-en-1-yl)-3-(methylsulfonyl)benzonitrile
Reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[S:11]([CH3:14])(=[O:13])=[O:12])=O.[C:15]([OH:18])(=O)[CH3:16].[NH:19]1CCC[CH2:21][CH2:20]1.O>ClCCl>[C:20]([C:21]([C:15](=[O:18])[CH3:16])=[CH:1][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[S:11]([CH3:14])(=[O:13])=[O:12])#[N:19]Participants
Procedure
4-Formyl-3-(methylsulfonyl)benzonitrile (3.0 g, 14.34 mmol) and sodium 1-cyanoprop-1-en-2-oxide (1.66 g, 15.8 mmol, 1.1 eq.; cf. R. Troschütz, Archiv der Pharmazie 1984, 317, 709-713) were initially charged in dichloromethane (180 ml). Glacial acetic acid (1.03 ml, 18 mmol, 1.25 eq.) and piperidine (142 μl, 1.43 mmol, 0.1 eq.) were then added, and the mixture was heated under reflux on a water separator (18 h). The reaction solution was then washed once with water (50 ml) and twice with saturated sodium bicarbonate solution (100 ml each), dried over sodium sulfate and concentrated. The solid residue was suspended in six times the amount of ethanol and once more filtered off with suction, and the crystals were washed with ethanol and dried under high vacuum. This gave 2.7 g (70% pure, 48% of theory) of the title compound.
Workup
- temperaturethe mixture was heated
- washThe reaction solution was then washed once with water (50 ml) and twice with saturated sodium bicarbonate solution (100 ml each)
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- filtrationonce more filtered off with suction
- washthe crystals were washed with ethanol
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-36cadde4a41a484aa9f22f58799dfdc9
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569314B2
Reaction notes
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