反应详情

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°.

1. waitat 60° for 23 hours
2. customthe precipitate that separated
3. customcollected on
4. filtrationa filter
5. washwashed with 50 ml of ethyl acetate
6. extractionThe combined filtrate and washings were extracted with 6×25 ml of saturated NaCl solution
7. customthe ethyl acetate evaporated