Sodium hydride → N-(2-azidopyridin-4-yl)-2,4,6-trichlorobenzamide

HRID 449913Notes

Reaction equation

[N:1]([C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][N:5]=1)=[N+:2]=[N-:3].[H-].[Na+].[Cl:13][C:14]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[C:15]=1[C:16](Cl)=[O:17]>CN(C=O)C.O>[N:1]([C:4]1[CH:9]=[C:8]([NH:10][C:16](=[O:17])[C:15]2[C:19]([Cl:24])=[CH:20][C:21]([Cl:23])=[CH:22][C:14]=2[Cl:13])[CH:7]=[CH:6][N:5]=1)=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 25 °C

Procedure

To a cooled (0° C.) solution of 2-azidopyridin-4-amine (500 mg, 3.7 mmol) in dry DMF (10 ml) was added NaH (178 mg, 7.4 mmol). After stirring for 10 min, a solution 2,4,6-trichlorobenzoyl chloride (1.8 g, 7.4 mmol) in DMF (5 mL) was added dropwise. The reaction was warmed to 25° C. and stirring was continued for 30 min. The reaction was diluted with water (50 mL) and extracted with ethyl acetate (3×10 mL). The combined organic extracts were washed with water (20 mL), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica-gel chromatography (petroleum ether/ethyl acetate=1:1) to afford N-(2-azidopyridin-4-yl)-2,4,6-trichlorobenzamide (180 mg, yield: 14%). LCMS (ESI) m/z: 342.0 [M+H+].

Workup

stirringstirring
waitwas continued for 30 min
extractionextracted with ethyl acetate (3×10 mL)
washThe combined organic extracts were washed with water (20 mL)
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe residue was purified by silica-gel chromatography (petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record: ord-1edab034f4564c2aba3d951058952577
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486950B2

Reaction notes

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