反应详情

Under an atmosphere of nitrogen gas, a mixture of 17 g (0.0085 mol) of 4-amino-N,N-dimethylbenzenesulfonamide, 25.5 ml (0.229 mol) of propargyl bromide, and 20.4 ml (0.175 mol) of 2,6-lutidine in 250 ml of N,N-dimethylacetamide is stirred at 90° for three and one-half hours, allowed to cool, and concentrated in vacuo. The concentrate is taken up in dichloromethane and water; the organic layer is separated, washed with brine, dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue is chromatographed over 1.1 kg of silica gel with a gradient of ethyl acetate in toluene of 10 to 15% to give 12.2 g of product, Rf (10% methanol/dichloromethane)≃0.84. Recrystallization from ethanol affords 10.2 g (50%) of product, as off-white crystals; mp 128°-131° C.

1. temperatureto cool
2. concentrationconcentrated in vacuo
3. customthe organic layer is separated
4. washwashed with brine
5. dry with materialdried (magnesium sulfate)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue is chromatographed over 1.1 kg of silica gel with a gradient of ethyl acetate in toluene of 10 to 15%