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

HRID 719868Notes

Reaction equation

C(N)(=O)C.Br[C:6]1[CH:7]=[CH:8][C:9]([N+:12]([O-:14])=[O:13])=[N:10][CH:11]=1.[CH3:15][S:16]([NH2:19])(=[O:18])=[O:17].C(=O)([O-])[O-].[K+].[K+].Cl>O>[N+:12]([C:9]1[N:10]=[CH:11][C:6]([NH:19][S:16]([CH3:15])(=[O:18])=[O:17])=[CH:7][CH:8]=1)([O-:14])=[O:13]

Participants

Conditions

Temperature: 145 °C

Procedure

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.

Workup

customwas quickly brought to 145° C
temperatureAt this time, the reaction was cooled to 25° C.
temperatureThis solution was cooled to 0° C.
customThe precipitate which resulted
customwas removed by filtration
additionThe filtrate was adjusted to pH=4 by the addition of a 1N aqueous hydrochloric acid solution
customThe resulting precipitate was collected
customdried in vacuo

Sources & evidence

ORD record: ord-6d6bdc4f7762442ca99a9597415bccb6
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132425B2

Reaction notes

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