反应详情

To 13 ml of 70% nitric acid in 100 ml of water was added 15.17 g (50.0 mmol) of the -toluenesulfonate obtained in step A, followed by the addition of 100 ml of glacial acetic acid and 0.37 g (5.0 mmol) of sodium nitrite. The mixture was heated on a steam bath for 1.5 hrs, cooled, diluted with 250 g of ice, and the precipitate was collected to yield 8.82 g of crude product. The crude product was chromatographed on 300 g of silica gel with 5:1 and 3:1 hexane:ethyl acetate to yield 6.30 g (36.2%) of 2,6-diethyl-4-nitrophenyl-p-toluenesulfonamide. NMR (CDCl3):δ 1.10 (t, 6H), 2.5 (m, 7H), 6.5 (s, 1H), 7.2-7.7 (dd, 4H), 7.97 (s, 2H).

1. temperatureThe mixture was heated on a steam bath for 1.5 hrs
2. temperaturecooled
3. customthe precipitate was collected
4. customto yield 8.82 g of crude product
5. customThe crude product was chromatographed on 300 g of silica gel with 5:1 and 3:1 hexane