Sulfuric Acid → Chloro-5-[(methylsulfonimidoyl)methyl]pyridine

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 2-chloro-5-[(methylsulfinyl)methyl]pyridine (B) (7.34 g, 39 mmol) and sodium azide (4.04 g, 62 mmol) in chloroform (80 mL) cooled to 0° C. was slowly added sulfuric acid at a rate such that the temperature did not rise above 8° C. After the addition was over, the ice-water bath was removed and the mixture was heated at 55° C. for 2.5 h. The solvent was decanted into a separation funnel and the residue was stirred and dissolved in water. After a few minutes, the aqueous mixture was made basic to pH 8 by slowly adding solid Na2CO3 and then saturated with solid NaCl. The extra salt was removed by filtration (a portion of the filtrate was sucked into trap and was not recovered) and the filtrate was extracted with CH2Cl2 three times. The combined organic layer was dried over Na2SO4, filtered, concentrated and the residue was triturated in CH2Cl2-ether (1:10, v/v) solvent. The white solid was filtered, washed with CH2Cl2-ether (1:10, v/v) and dried to give 2.70 g of -chloro-5-[(methylsulfon-imidoyl)methyl]pyridine (C) in 34% yield as a white solid (m.p. 134.5-136° C.). LC-MS (ELSD): mass calcd for C7H9ClN2OS [M+H]+ 203.67. Found: 203.22.

Provenance & Evidence