Sulfuric Acid → HCID 59215215, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH3:14])[CH2:10][S:11]([CH3:13])=[O:12])=[CH:4][N:3]=1.[N-:15]=[N+]=[N-].[Na+].OS(O)(=O)=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH3:14])[CH2:10][S:11]([CH3:13])(=[NH:15])=[O:12])=[CH:4][N:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
To a stirred mixture of 2-chloro-5-[2-methyl-3-(methylsulfinyl)propyl]-pyridine (2.15 g, 9.3 mmol) and sodium azide (1.81 g, 28 mmol) in chloroform (30 mL) cooled in an ice-water bath was added concentrated H2SO4 (6 mL) and the resulting mixture stirred at this temperature for 10 min. The reaction was then heated at 55° C. in an oil-bath for 16 hrs. Upon cooling down, the mixture was diluted with ice-water (70 mL) and the organic layer removed. The aqueous phase was washed with CH2Cl2 (2×30 mL) and the organic phase was discarded. The aqueous phase was made basic by the careful addition of aqueous ammonia whereupon an oil separated, which was extracted with CH2Cl2 (2×30 mL). The combined organic phase was dried over MgSO4 and solvent evaporated to give 2.15 g of the product as a yellowish oil in 94% yield. [M+H]+=247, 249; δ 1.11 (overlapping d, 3H).
Workup
- temperaturecooled in an ice-water bath
- temperatureUpon cooling down
- customthe organic layer removed
- washThe aqueous phase was washed with CH2Cl2 (2×30 mL)
- additionThe aqueous phase was made basic by the careful addition of aqueous ammonia whereupon an oil
- customseparated
- extractionwhich was extracted with CH2Cl2 (2×30 mL)
- dry with materialThe combined organic phase was dried over MgSO4 and solvent
- customevaporated
Sources & evidence
- ORD record
- ord-1fd57a481338478ba6ac42a9c578bdcb
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834188B2
Reaction notes
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