Reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:11])=[CH:5][C:6]=1[S:7]([Cl:10])(=[O:9])=[O:8].[S][Cl:13].O>S(Cl)(Cl)(=O)=O.[Cl-].[Cl-].[Cl-].[Al+3]>[Cl:1][C:2]1[S:3][C:4]([Cl:11])=[C:5]([Cl:13])[C:6]=1[S:7]([Cl:10])(=[O:8])=[O:9]Participants
6
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 2,5-dichlorothiophene-3-sulfonyl chloride (1.2 g, 5 mmol) and sulfur monochloride (10 mg) in sulfuryl chloride (500 mg) was heated at 60° C. for 30 min, at which time was added dropwise a mixture of aluminum trichloride (10 mg) in sulfuryl chloride (500 mg). The reaction was heated at 60° C. for an additional 3 hours, at which time it was allowed to cool to ambient temperature. Cold water (20 mL) was added and the reaction extracted with dichloromethane (2×20 mL). The combined organic layers were washed with saturated sodium bicarbonate solution, dried (Mg2SO4) and concentrated to furnish a tan solid (420 mg, 33%).
Workup
- additionwas added dropwise
- temperatureThe reaction was heated at 60° C. for an additional 3 hours, at which time it
- temperatureto cool to ambient temperature
- extractionthe reaction extracted with dichloromethane (2×20 mL)
- washThe combined organic layers were washed with saturated sodium bicarbonate solution
- dry with materialdried (Mg2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2f30ba84e4194cd6b9cb4784c4f11ab7
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091204B2
Linked notes
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