Benzene → 2-Trifluoromethyl-9-chloro-11-chloro-10,11-dihydrodibenzo[b,f]thiepin
Reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:19]=[CH:18][C:6]2[S:7][C:8]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:9]=3[CH2:10][CH:11](O)[C:5]=2[CH:4]=1.C1C=CC=CC=1.S(Cl)([Cl:30])=O>N1C=CC=CC=1.O>[F:1][C:2]([F:21])([F:20])[C:3]1[CH:19]=[CH:18][C:6]2[S:7][C:8]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:9]=3[CH2:10][CH:11]([Cl:30])[C:5]=2[CH:4]=1Participants
Procedure
To the mixture of 0.5 g of 2-trifluoromethyl-9-chloro-10,11-dihydrodibenzo[b,f]thiepin-11-ol, 5 ml of anhydrous benzene and one drop of anhydrous pyridine were added dropwise with stirring 0.3 g of thionyl chloride with ice-cooling and the resulting mixture was reacted at room temperature for 10 minutes, then refluxed for 20 minutes, and freed of benzene under reduced pressure. To the thus obtained residue was added water and the mixture was extracted with benzene. The extract was washed with water, saturated sodium bicarbonate, then water, dried over anhydrous sodium sulfate and freed of benzene to obtain 2-trifluoromethyl-9-chloro-11-chloro-10,11-dihydrodibenzo[b,f]-thiepin as colorless crystals having a melting point of 88°-90° C.
Workup
- additionwere added dropwise
- temperaturecooling
- customthe resulting mixture was reacted at room temperature for 10 minutes
- temperaturerefluxed for 20 minutes
- extractionthe mixture was extracted with benzene
- washThe extract was washed with water, saturated sodium bicarbonate
- dry with materialwater, dried over anhydrous sodium sulfate
Sources & evidence
- ORD record
- ord-fe51f5bfe845444a8602c40f25396e96
- Source dataset
- uspto-grants-1979_08
- Patent number
- US04166127
Reaction notes
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