Hydrochloric Acid → 6-Chloro-5-methylpyridine-3-sulfonyl chloride
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5](N)=[CH:4][C:3]=1[CH3:9].[ClH:10].N([O-])=O.[Na+].[S:15](=[O:17])=[O:16]>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:15]([Cl:10])(=[O:17])=[O:16])=[CH:4][C:3]=1[CH3:9]Participants
Procedure
Under ice-cooling, thionyl chloride (0.6 mL) was added dropwise over 30 min to water (3.4 mL). The mixture was stirred at room temperature for 12 hr to give a sulfur dioxide-containing solution. Separately, under ice-cooling, 6-chloro-5-methylpyridine-3-amine (278 mg) was added to concentrated hydrochloric acid (6 mL) and the mixture was stirred. An aqueous solution (2 mL) of sodium nitrite (148 mg) was added dropwise while keeping the inside temperature at not higher than 5° C., and the mixture was further stirred for 15 min. The reaction mixture was gradually added at 5° C. to the above-mentioned sulfur dioxide-containing solution added with cuprous chloride (5 mg). Under ice-cooling, the mixture was further stirred for 30 min, and the precipitate was collected by filtration and washed with water to give the title compound as a pale-yellow solid (yield 271 mg, 62%).
Workup
- additioncontaining solution
- temperatureSeparately, under ice-cooling
- customhigher than 5° C.
- stirringthe mixture was further stirred for 15 min
- additioncontaining solution
- temperatureUnder ice-cooling
- stirringthe mixture was further stirred for 30 min
- filtrationthe precipitate was collected by filtration
- washwashed with water
Sources & evidence
- ORD record
- ord-2b4cc76b6b5a4ff3a491f3454b1467ec
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299261B2
Reaction notes
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