反应详情

2-chloro-3-(4-methoxybenzenesulfonyl)-6-methylpyridine (1.6 g, 5.39 mmol) and 2,4,6-trimethylaniline (4.4 g, 32.8 mmol) were heated at reflux in ethylene glycol (5.5 mL) for 20 h. After cooling, the reaction was partitioned between EtOAc (100 mL) and 0.5 N NaOH (20 mL) and the aqueous layer was extracted with EtOAc (100 mL) and the combined organic extracts were washed with water, brine, dried and stripped in vacuo. The residue was chromatographed on silica gel using 20% EtOAc/hexanes as eluent to give [3-(4-methoxybenzenesulfonyl)-6-methyl-pyridin-2-yl]-(2,4,6-trimethylphenyl)-amine as a solid (1.4 g), mp 165–167° C. mass spec. (AP+): m/z 397 (M+1).

1. temperatureAfter cooling
2. customthe reaction was partitioned between EtOAc (100 mL) and 0.5 N NaOH (20 mL)
3. extractionthe aqueous layer was extracted with EtOAc (100 mL)
4. washthe combined organic extracts were washed with water, brine
5. customdried
6. customThe residue was chromatographed on silica gel using 20% EtOAc/hexanes as eluent