Hydrochloric Acid → 5,6-dichloropyridine-3-sulfonyl Chloride
Reaction equation
N([O-])=O.[Na+].[ClH:5].[Cl:6][C:7]1[CH:8]=[C:9](N)[CH:10]=[N:11][C:12]=1[Cl:13].[S:15]([O-:18])([O-])=[O:16].[Na+].[Na+]>S([O-])([O-])(=O)=O.[Cu+2].O>[Cl:6][C:7]1[CH:8]=[C:9]([S:15]([Cl:5])(=[O:18])=[O:16])[CH:10]=[N:11][C:12]=1[Cl:13]Participants
Procedure
With cooling with ice, an aqueous solution (2.5 ml) of sodium nitrite (1.1 g, 16.0 mmol) was added to a hydrochloric acid solution (15 ml) of 5,6-dichloropyridine-3-amine (2.0 g, 12.3 mmol), stirred for 30 minutes, and the reaction solution was filtered. The filtrate was added to a mixed hydrochloric acid (35 ml)/water (8 ml) solution of sodium sulfite (3.87 g, 30.7 mmol) and copper sulfate (0.29 g, 1.84 mmol) along with an aqueous solution (8 ml) of sodium sulfite (3.87 g, 30.7 mmol) thereto, with cooling with ice, and stirred for 30 minutes. The reaction solution was extracted with chloroform, the organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 5,6-dichloropyridine-3-sulfonyl chloride (2.41 g, yield: 80%) as a brown oil.
Workup
- temperatureWith cooling with ice
- filtrationthe reaction solution was filtered
- temperaturewith cooling with ice
- stirringstirred for 30 minutes
- extractionThe reaction solution was extracted with chloroform
- washthe organic layer was washed with saturated saline water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-313fa2da02c848059a0767f5b16b8e10
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846700B2
Reaction notes
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