Dimethylformamide → p-Cyanobenzenesulphonamide

HRID 656265Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([S:8](=[O:11])(=[O:10])[NH2:9])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[CH3:17][N:18](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N>[C:17]([C:2]1[CH:7]=[CH:6][C:5]([S:8](=[O:11])(=[O:10])[NH2:9])=[CH:4][CH:3]=1)#[N:18]

Participants

Conditions

Temperature: 80 °C

Procedure

The compound 2-2 (58 mg) prepared in Step 1 was dissolved in dimethylformamide (2 ml) and to the solution were added zinc cyanide [Zn(CN)2] (58 mg) and tetrakistriphenylphosphine palladium (10 mg), followed by stirring at 80° C. for 12 hours. The resulting mixture was basified with aqueous sodium bicarbonate solution, diluted with ethyl acetate (30 ml), washed with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was chromatographed on silica gel column eluting with ethyl acetate/hexane (1/2) to yield the compound 2-3 (30 mg, 80%).

Workup

washwashed with water and saturated aqueous sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was chromatographed on silica gel column
washeluting with ethyl acetate/hexane (1/2)

Sources & evidence

ORD record: ord-c82a4e10cc164f899e84f51765052f35
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071650B2

Reaction notes

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