Sodium Iodide → N-(2-dimethylamino-ethyl)-N-methylsulphonyl-4-nitroaniline

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Reaction Steps

36.00 g (0.166 mol) of N-(4-nitro-phenyl)-methanesulphonic acid amide was dissolved in 2000 mL acetone. The solution was combined with 47.8 g (0.332 mol) of 1-chloro-2-dimethylaminoethane * HCl, 68.8 g (0.498 mol) of potassium carbonate, 5.0 g (0.033 mol) of sodium iodide and 50 mL water. It was refluxed for 16 hours with stirring. After the addition of another 23.9 g (0.166 mol) of 1-chloro-2-dimethylaminoethane * HCl, 45.9 g (0.332 mol) of potassium carbonate and 5.0 g (0.033 mol) of sodiumiodide, the mixture was refluxed for 5 hours with stirring. At RT the inorganic salts were filtered off. The filtrate was evaporated down i. vac. and the residue dissolved in EtOAc. The org. phase was washed 2× with semisat. aqueous sodium chloride solution, dried over magnesium sulphate, filtered and evaporated down i. vac.

Provenance & Evidence