Sulfuric Acid → HCID 59215215, compound

Participants

Reaction Conditions

Reaction Steps

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; δ1.11 (overlapping d, 3H).

Provenance & Evidence