Acetamide → N-(6-nitropyridin-3-yl)methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

A solution of molten acetamide (2.36 g, 40.0 mmol) heated to 90° C. was treated with a mixture of 5-bromo-2-nitropyridine (2.0 g, 9.85 mmol), methanesulfonamide (2.81 g, 29.55 mmol), and potassium carbonate (3.43 g, 24.8 mmol). The resulting mixture was quickly brought to 145° C. The resulting solution was stirred at 145° C. for 30 min. At this time, the reaction was cooled to 25° C. and then was treated with water (8 mL). This solution was cooled to 0° C. and then was treated with a 1N aqueous hydrochloric acid solution until the pH of the solution was adjusted to pH=8. The precipitate which resulted was removed by filtration. The filtrate was adjusted to pH=4 by the addition of a 1N aqueous hydrochloric acid solution. The resulting precipitate was collected and dried in vacuo to afford N-(6-nitro-pyridin-3-yl)-methanesulfonamide (1.46 g, 68%) as a white solid: mp 187–189° C.; (ES)−-HRMS m/e calcd for C6H7N3O4S (M−H)− 216.0084, found 216.0085.

Provenance & Evidence