Nitrogen → N,N-Dimethyl-2-[N-(3-hydroxypropyl)-N-methylaminosulfonyl]-6-nitrobenzamide

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Reaction Steps

N,N-Dimethyl-2-[N-(3-hydroxypropyl)aminosulfonyl]-6-nitrobenzamide (1.37 g, 4.13 mmol) in 12 ml of DMF, was added dropwise to a suspension of 198 mg (4.13 mmol) of 50% NaH in 3 ml of DMF in an atmosphere of N2. When evolution of hydrogen was complete, a solution of methyl p-toluene sulfonate (0.794 g, 4.14 mmol) in DMF, 2 ml, was added. The clear deep Yellow solution was stirred at 25° for 17 hours, then at 60° for 23 hours. The solution then was mixed with 175 ml of ethyl acetate and the precipitate that separated collected on a filter and washed with 50 ml of ethyl acetate. The combined filtrate and washings were extracted with 6×25 ml of saturated NaCl solution and the ethyl acetate evaporated to give 1.66 g of a clear yellow oil. Flash chromatography over E. Merck silica gel 60 (230-400 mesh) gave 0.49 g of a clear light yellow oil. This material was dissolved in 50 ml of CHCl3, the solution extracted with 4×5 ml of lN NaOH, then with 3 x 5 ml of saturated NaCl and dried over MgSO4.After evaporation of the CHCl3, the residue was dissolved in ethyl acetate and the solution filtered to remove a trace of MgSO4. Evaporation of the solvent gave 0.44 g of light yellow crystalline product, m.p., 91.5°-92.5°.

Provenance & Evidence