Sulfuryl chloride → N-(Methylsulfonyl)-2-(chloronitromethylene)-tetrahydro-2H-1,3-thiazine

Participants

Reaction Steps

A solution of 1.25 g of redistilled sulfuryl chloride in 5 ml of methylene chloride was added drop-by-drop over a 5-minute period to a slurry of (1A) in 50 ml of methylene chloride in a nitrogen atmosphere at 0-5° C. The mixture was stirred for 30 minutes more, then allowed to warm to room temperature. Two drops more of sulfuryl chloride were added and the mixture was stirred for 5 minutes. The resulting mixture was washed with water, then with brine, dried (MgSO4), and stripped of solvent to give a yellow solid. The solid was triturated with ether to give (2), as a yellow solid, m.p. 149°-151° C. (with decomposition).

Provenance & Evidence