Thionyl Chloride → 7-chloro-3-(4-chlorophenyl)-2,3-dihydro-4H-1-benzothiopyran-4-one
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][S:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:9]([OH:11])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O>CN(C)C=O.CCCCCC>[Cl:20][C:16]1[CH:17]=[CH:18][C:19]2[C:9](=[O:11])[CH:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:12][S:13][C:14]=2[CH:15]=1Participants
Procedure
A solution of 4-chlorophenyl-α-[(3-chlorophenyl)thiomethyl]acetic acid (2.0 g), thionyl chloride (5 ml) and N,N-dimethylformamide (one drop) in hexane (10 ml) was heated at reflux for 1 hour. The reaction mixture was concentrated under reduced pressure. To the resulting residue, dichloroethane (13 ml) was added under a stream of nitrogen gas and anhydrous aluminum chloride (1.0 g) was added in small portions at a temperature below 0° C. The reaction was allowed to proceed at 0° C. for 1 hour, and the reaction mixture was poured into ice-water and extracted with methylene chloride (100 ml, 50 ml×2). The extract was dried over anhydrous magnesium sulfate and concentrated to give 7-chloro-3-(4-chlorophenyl)-2,3-dihydro-4H-1-benzothiopyran-4-one.
Workup
- temperatureat reflux for 1 hour
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionTo the resulting residue, dichloroethane (13 ml) was added under a stream of nitrogen gas and anhydrous aluminum chloride (1.0 g)
- additionwas added in small portions at a temperature below 0° C
- additionthe reaction mixture was poured into ice-water
- extractionextracted with methylene chloride (100 ml, 50 ml×2)
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-eca052c980ba45f59c2bdcc4cbfd4c8d
- Source dataset
- uspto-grants-1995_09
- Patent number
- US05451607
Reaction notes
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