4-Aminopyridine → Methanesulfonamide, N-4-pyridinyl-

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Reaction Steps

9.9 g of 4-aminopyridine (104.8 mmol) and 14.5 ml of triethylamine (10.6 g, 104.8 mmol) were dissolved at room temperature in 72 ml of dimethylformamide. Likewise at room temperature, 8.1 ml of methanesulphonyl chloride (12.0 g, 104.8 mmol) were added dropwise to this solution over the course of one hour. The exothermic reaction meant that the temperature had to be maintained by ice bath cooling. After 20 h of stirring at room temperature the solvent was distilled off in vacuo. The residue which remained was taken up in 100 ml of methylene chloride and in 150 ml of 1 N NaOH. The organic phase was separated off. The aqueous phase was adjusted cautiously to a pH of 4admixed with 100 ml of EtOH and 100 ml of methylene chloride. After the organic phase had been separated off, the aqueous phase was further admixed three times with 100 ml of EtOH and 100 ml of methylene chloride. The collected organic phases were freed from the solvent, and the crude product which remained was recrystallized from acetonitrile. This gave 3.2 g of product. The constitution of the compound was verified by NMR spectroscopy.

Provenance & Evidence