2-Nitropropane → HCID 14622559, compound

Participants

Reaction Steps

A solution of N-(2-dimethylaminoethyl)-N-methyl-4-chloro-3-nitrobenzenesulfonamide base (15.65 g, 49 mmol) and the lithium salt of 2-nitropropane (4.66 g, 49 mmol) in dimethylsulfoxide (100 mL) was stirred under nitrogen at 20°-25° for 3 days. An additional 0.35 g of the lithium salt was then added and stirring continued for three days more. After pouring the reaction mixture on ice, product was extracted into a 1:1 mixture of ethyl acetate and toluene which was washed with water, dried (Na2SO4), filtered and concentrated. Flash chromatography of the residue over silica gel and elution with 3% methanol-97% methylene chloride afforded 2.0 g of product. Treatment with anhydrous ethanolic hydrogen chloride and recrystallization from methanol-ethyl acetate hexane gave the hydrochloride salt, m.p. 231°-32.5° dec.

Provenance & Evidence