N-methyl-2-pyrrolidone → 2-Trifluoromethyl-9-cyano-10,11-dihydrodibenzo[b,f]thiepin
Reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:18]=[CH:17][C:6]2[S:7][C:8]3[CH:15]=[CH:14][CH:13]=[C:12](Cl)[C:9]=3[CH2:10][CH2:11][C:5]=2[CH:4]=1.[Cu](C#N)[C:22]#[N:23].CN1CCCC1=O.O.N>S([O-])([O-])(=O)=O.[Cu+2].O>[F:1][C:2]([F:20])([F:19])[C:3]1[CH:18]=[CH:17][C:6]2[S:7][C:8]3[CH:15]=[CH:14][CH:13]=[C:12]([C:22]#[N:23])[C:9]=3[CH2:10][CH2:11][C:5]=2[CH:4]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
The mixture of 450 mg of 2-trifluoromethyl-9-chloro-10,11-dihydrodibenzo[b,f]thiepin, 0.4 g of copper cyanide, 0.05 g of anhydrous copper sulfate and 10 ml of N-methylpyrrolidone was stirred at 180° to 210° C. for 18.5 hrs. while preventing the moisture. After cooling, to the mixture was added 2.5 ml of conc. ammonia water and 35 ml of water and the resulting mixture was filtered with the use of celite. The thus obtained solution was extracted with benzene and the extract was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 0.3 g of a brown oily substance, which was chromatographed on a silica gel, eluted with n-hexane, and there was obtained 64 mg of the desired product. This was recrystallized from n-hexane to afford 2-trifluoromethyl-9-cyano-10,11 -dihydrodibenzo[b,f]thiepin having a melting point of 113° to 114.5° C. as colorless crystals.
Workup
- temperatureAfter cooling, to the mixture
- filtrationthe resulting mixture was filtered with the use of celite
- extractionThe thus obtained solution was extracted with benzene
- washthe extract was washed with water
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated
- customto obtain 0.3 g of a brown oily substance, which
- customwas chromatographed on a silica gel
- washeluted with n-hexane
Sources & evidence
- ORD record
- ord-de4906c2a94047a598554ec71d34152d
- Source dataset
- uspto-grants-1979_08
- Patent number
- US04166127
Reaction notes
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